Positive allosteric modulators of sweet taste

ABSTRACT

The invention provides compounds as allosteric modulators that are useful as sweet flavor enhancers. The present invention also includes ingestible compositions comprising the present compounds and methods of enhancing the sweet taste of sweeteners and sugars.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority benefit of U.S. Provisional PatentApplication No. 62/807,675, filed Feb. 19, 2019, the disclosure of whichis incorporated herein by reference in its entirety.

FIELD OF THE INVENTION

The present disclosure relates generally to compounds for enhancingsweet taste, ingestible compositions containing these compounds, andmethods of using and preparing such compositions.

BACKGROUND

Living things use sensory systems to detect important information aboutthe environment in which they live. Taste is a particularly importantsensory system, and is one of the most sophisticated forms ofchemically-triggered sensations found throughout the animal kingdom.

Mammals are believed to have five basic taste modalities: sweet, bitter,sour, salty, and umami (savory). The pleasant taste associated withsweetness is important in industries that produce consumable materials.Natural sugars, such as sucrose, fructose, and glucose, for example, areheavily utilized by the beverage, food, pharmaceutical, and oralhygienic/cosmetic industries. However, many consumers are required tocontrol or reduce the sugar and calorie content of their diets due tohealth concerns such as obesity, diabetes, and heart disease. Thus,there is a continuing need in the market to provide alternative,non-caloric or low-caloric sweeteners with sugar-like taste forconsumers who need or desire to limit caloric intake.

One option for addressing this need is the use of natural high-potencysweeteners (NHPS). Because these sweeteners are many times sweeter thansucrose, for example, much less of the sweetener is required to replacethe sugar; however, these sweeteners often possess taste qualities thatvary from those of natural sugars. For example, certain sweeteningcompositions have different temporal profiles, maximal responses, flavorprofiles, mouthfeel, and/or adaptation behaviors from those of sugar. Inaddition, high-potency sweeteners generally exhibit bitter, metallic,cooling, astringent, or licorice-like aftertastes, and/or diminishingsweetness on iterative tasting. These properties can be undesirable forconsumers.

Therefore, improved compounds and methods for enhancing the sweetness ofconsumable materials, while retaining the characteristics of sugar andkeeping calorie content low, are desired.

It is known that sensations associated with taste involve distinctsignaling pathways mediated by receptors, which specifically recognizemolecules that elicit those taste sensations. Recent developments insweetening methods include the use of certain molecules that enhance thesweet taste of existing sweeteners and sugars, rather than acting assweeteners themselves. The following disclosure provides new, naturaland/or unnatural compounds as positive modulator compounds for enhancingsweet taste.

BRIEF SUMMARY

The present invention provides isolated compounds for enhancing sweettaste, ingestible compositions containing these compounds, and methodsof using and preparing such ingestible compositions, to help meet theneed for improved consumer-friendly, low-calorie sweetened products.

The present invention further provides improved methods of enhancing,modulating, or potentiating the perception, by a subject, of the sweettaste of an ingestible composition, such as a food, beverage, orpharmaceutical product.

Further provided are improved methods for modulating, particularlyenhancing or potentiating, the activation of a sweet taste receptor.

Embodiments of the invention provide compounds as sweet taste modulatorsthat enhance sweet taste receptor activity and sweetness perceptionwhile reducing the required concentration of, for example, an artificialsweetener or sugar. In certain embodiments, the sweet taste modulator isany one of the compounds from Table 1 and Table 2 (e.g., the compoundsof Table 3), or a combination thereof, or a salt or derivative thereof.

The sweet taste modulator can be combined with any suitable sugar orsweetener, such as, for example, a natural caloric sweetener; a naturalhigh-potency sweetener; a synthetic sweetener, including synthetichigh-potency sweeteners; sugar alcohols; rare sugars; sweetenerenhancers; or combinations thereof, to provide an ingestible compositionhaving enhanced sweetness.

In another embodiment, the present invention provides a method ofincreasing the sweet taste of an ingestible composition by adding acompound of the present invention to the ingestible composition. Thecompound used according to the current invention can be a chemosensoryreceptor modifier, a chemosensory receptor ligand modifier, or both,e.g., a partial chemosensory receptor modifier and partial chemosensoryreceptor ligand modifier. For example, the compound of the presentinvention can be a sweet receptor agonist, or a sweet enhancer, or apartial sweet receptor agonist and partial sweet enhancer.

In another embodiment, the present invention provides an ingestiblecomposition comprising the sweet taste modulator and aningestibly-acceptable excipient. According to particular embodiments,the ingestible composition can be a product selected from beverages,foods, pharmaceuticals, tobacco products, oral hygienic/cosmetics,nutraceuticals, and the like.

In yet another embodiment, the present invention provides a flavoringconcentrate formulation comprising a compound of the present inventionas a flavor modifying ingredient, a carrier, and optionally, at leastone adjuvant.

DETAILED DISCLOSURE

The present invention provides isolated compounds for enhancing sweettaste, ingestible compositions containing such compounds, and methods ofpreparing such ingestible compositions to help meet the need forimproved low-calorie sweetened products.

The present invention further provides improved methods of enhancing,modulating, and/or potentiating the sweet taste of an ingestiblecomposition, such as a food, beverage, or pharmaceutical product. Thepresent invention also provides an improved method of modulating,particularly enhancing or potentiating, the activation of a sweet tastereceptor.

The compounds of the invention include all stereochemical forms of thecompound, including geometric isomers (i.e., E, Z) and optical isomers(i.e., R, S). Single stereochemical isomers as well as enantiomeric anddiastereomeric mixtures of the present compounds are specificallycontemplated. The compounds may also exist in several tautomeric forms.The term “tautomer” as used herein refers to isomers that change intoone another with great ease such that they can exist together inequilibrium. Accordingly, the chemical structures depicted hereinencompass all possible tautomeric forms of the illustrated compounds.Additionally, unless otherwise stated, formulas depicted herein are alsomeant to include compounds that differ only in the presence of one ormore isotopically enriched atoms.

Further included within the scope of the present invention are variousforms and derivatives of the exemplified compounds. Such forms include,but are not limited to, unsolvated, solvated, and hydrated forms.Further, derivative forms include, but are not limited to, acylatedderivatives, alkylated derivatives, amidated derivatives, esterifiedderivatives, and other like derivatives. Furthermore, the compounds mayexist in multiple crystalline or amorphous forms. In general, allphysical forms are contemplated herein and are within the scope of thepresent invention.

Selected Definitions

As used herein, an “ingestible composition” includes any substance that,either alone or together with another substance, can be ingested orally,whether intended for consumption or not. Ingestible compositionsinclude, for example, “food or beverage products,” “pharmaceuticals,” aswell as “non-edible products.” By “food or beverage products,” it ismeant any edible product intended for consumption by humans or animals,including solids, semi-solids, and liquids (e.g., beverages). The term“non-edible products” or “non-comestible composition” includes anyproduct or composition that can be taken orally by humans or animals forpurposes other than consumption as food or beverage. For example,non-edible products and noncomestible compositions includepharmaceuticals and over the counter medications, oral care productssuch as dentifrices and mouthwashes, cosmetic products such as sweetenedlip balms and other personal care products.

An “ingestibly acceptable carrier or excipient” is a medium and/orcomposition that is used to prepare a desired form of an inventivecompound of the subject invention, in order to administer the compound.The medium and/or composition may be in any form depending on theintended use of a product, e.g., solid, semi-solid, liquid, paste, gel,cream, foamy material, suspension, solution, or any combination thereof(such as a liquid containing solids). Ingestibly acceptable carriersinclude many common food ingredients, such as water at neutral, acidic,or basic pH; fruit or vegetable juices; vinegar; marinades; beer, wine;natural water/fat emulsions such as milk or condensed milk; edible oilsand shortenings; fatty acids and their alkyl esters; low molecularweight oligomers of propylene glycol; glyceryl esters of fatty acids;and dispersions or emulsions of such hydrophobic substances in aqueousmedia; salts such as sodium, calcium or potassium chloride; wheatflours; solvents such as ethanol; solid edible diluents such asvegetable powders or flours; other liquid vehicles; dispersion orsuspension aids; surface active agents; isotonic agents; thickening oremulsifying agents; preservatives; solid binders; lubricants and thelike.

According to the present invention, a “chemosensory receptor” can be anyreceptor associated with chemosensory sensation or chemosensory ligandtriggered signal transduction, e.g., via taste receptors ortaste-related receptors expressed in taste buds or internal organs ofthe body, such as in the gastrointestinal tract, etc. In one embodiment,a chemosensory receptor is a receptor that belongs to the7-transmembrane receptor superfamily or G protein-coupled receptors(GPCRs). In another embodiment, a chemosensory receptor is a receptorcarrying out signal transduction via one or more G proteins. In yetanother embodiment, a chemosensory receptor is a receptor that belongsto family C or class C of GPCRs. In yet another embodiment, achemosensory receptor is a receptor that belongs to the TIR family. Inyet another embodiment, a chemosensory receptor is a receptor of TIR1,TIR2, TIR3, or their equivalents or variants or a combination thereof.In still another embodiment, a chemosensory receptor is a hetero-dimerof TAS1R2 and TAS1R3, or their equivalent or variant.

An “enhancer” refers to a compound that modulates (increases) theactivation of a particular receptor, preferably a chemosensory, e.g.,the TAS1R2/TAS1R3 receptor. Such enhancers typically enhance theactivation of a chemosensory receptor by its ligand. Typically the“enhancer” will be specific to a particular ligand, i.e., it will notenhance the activation of a chemosensory receptor by chemosensoryligands other than the particular chemosensory ligand, or ligandsclosely related thereto.

Some enhancers, at their ligand-enhancing concentration, do not resultin activation of the particular receptor by themselves. That is, theligand-enhancing concentrations of these enhancers are concentrationlevels of the enhancers that increase or enhance the activation of aparticular receptor by a ligand without substantially activating theparticular receptor by the enhancers themselves. In some embodiments,certain enhancers, when used at a concentration higher than theligand-enhancing concentration, can also activate a particular receptorby themselves in addition to modulating the activation of the receptor.For example, certain enhancers, when used at a concentration higher thanthe ligand-enhancing concentration, can be sweeteners (i.e., sweetflavoring agent/entity) as well. In other embodiments, certain enhancerscan activate a particular receptor by themselves in addition tomodulating the activation of the receptor simultaneously at the sameconcentration. In other words, certain enhancers are also sweeteners(i.e., sweet flavoring agent/entity) at the same time.

A “flavor” refers to the perception of taste in a subject, whichincludes sweet, sour, salty, bitter and umami. The subject may be ahuman or an animal.

A “flavoring agent” refers to a compound that induces a flavor or tastein an animal or a human. The flavoring agent can be natural,semi-synthetic, or synthetic.

A “flavor modifier” or “flavor modifying agent” refers to a compoundthat modulates, including enhancing or potentiating, and/or inducing,the tastes of a flavoring agent in an animal or a human.

A “flavor enhancer” refers to a compound that enhances the taste of aflavoring agent, or an ingestible composition comprising the flavoringagent.

A “sweet flavor” refers to the sweet taste typically induced by sugar,such as sucrose or fructose, in an animal or a human.

A “sweet flavoring agent,” “sweet flavor entity,” “sweetener,” or “sweetcompound” refers to a compound that elicits a detectable sweet flavor ina subject, e.g., fructose or a compound that activates a TAS1R2/TAS1R3receptor. The subject may be a human or an animal.

A “sweet flavor modifier” or “sweet flavor modifying agent” refers to acompound that modulates, including enhancing or potentiating, inducing,or blocking, the sweet taste of a sweet flavoring agent in an animal ora human. The sweet flavor modifier includes both sweet flavor enhancerand sweet flavoring agent.

A “sweet flavor enhancer” or “sweet flavor enhancing agent” refers to anenhancer of a sweet flavor.

A “sweet receptor activating compound” or “sweet receptor agonist”refers to a compound that activates a sweet receptor, such as, forexample, a TAS1R2/TAS1R3 receptor. One example of a sweet receptoractivating compound is a sweetener, such as sucrose or fructose.

A “sweet receptor modulating compound” refers to a compound thatmodulates (activates, blocks, or enhances/reduces activation of) a sweetreceptor such as a TAS1R2/TAS1R3 receptor.

A “sweet receptor enhancing compound” refers to a compound that enhancesor potentiates the effect of a sweet receptor activating compound.

A “sweet flavor modulating amount” refers to an amount of a compoundthat is sufficient to alter (either increase or decrease) sweet taste inan ingestible composition sufficiently to be perceived by a humansubject. In many embodiments of the invention, at least about 0.001 ppmof the compound would need to be present in order for most humansubjects to perceive a modulation of the sweet flavor of an ingestiblecomposition comprising the compound. A broad range of concentrationsthat can be employed in order to provide a desirable degree of sweetflavor modulation can be from about 0.001 ppm to 100 ppm, or a narrowrange from about 0.1 ppm to about 10 ppm. Alternative ranges of sweetflavor modulating amounts can be from about 0.01 ppm to about 30 ppm,from about 0.05 ppm to about 15 ppm, from about 0.1 ppm to about 5 ppm,or from about 0.1 ppm to about 3 ppm.

A “sweet flavor enhancing amount” refers to an amount of a compound thatis sufficient to enhance the taste of flavoring agents, e.g., sucrose orfructose, in an ingestible composition, as perceived by an animal or ahuman. A broad range of a sweet flavor enhancing amount can be fromabout 0.001 ppm to 100 ppm, or a narrow range from about 0.1 ppm toabout 10 ppm. Alternative ranges of sweet flavor enhancing amounts canbe from about 0.01 ppm to about 30 ppm, from about 0.05 ppm to about 15ppm, from about 0.1 ppm to about 5 ppm, or from about 0.1 ppm to about 3ppm. In some embodiments, sweet flavor enhancing amount is the amountcorresponding to ligand enhancing concentration(s) of a sweet flavorenhancer of the present invention.

A “sweet receptor modulating amount” refers to an amount of a compoundthat is sufficient to modulate (activate, enhance or block) a sweettaste receptor protein. In many embodiments of the invention, a sweetreceptor modulating amount is at least about 10 nM, at least about 100nM, at least about 1 μM, at least about 10 μM, at least about 100 μM, atleast about 1 mM, at least about 10 mM, or at least about 100 mM.

A “TAS1R2/TAS1R3 receptor modulating or activating amount” is an amountof compound that is sufficient to modulate or activate a TAS1R2/TAS1R3receptor.

A “sweet receptor” is a taste receptor that can be modulated by a sweetcompound. Preferably a sweet receptor is a G protein coupled receptor,and more preferably the sweet receptor is a TAS1R2/TAS1R3 receptor.

The terms “isolated,” and “purified,” refer to material that issubstantially or essentially free from components that normallyaccompany the compound as found in its native state. Purity andhomogeneity are typically determined using analytical chemistrytechniques. Particularly, in preferred embodiments, the compound is atleast 85% pure, more preferably at least 90% pure, more preferably atleast 95% pure, and most preferably at least 99% pure.

Compounds of the Current Invention

In specific embodiments, the present invention provides sweet tastemodulator compounds as shown in Table 1 and Table 2, as well asderivatives of the compounds exemplified in Table 1 and Table 2. Inpreferred embodiments, these compounds are isolated or purified.

TABLE 1 No. SMILES structures 1.Cc1c(c(c(c2c1OC[C@@H](C2=O)Cc1ccc(cc1O)O)O)OC)O 2.c12c(c(c(cc2O)O)C)occ(c1=O)Cc1c(c2c(cc1)OCO2)O 3.c12c(c(c(cc2O)O)OC)OC[C@H](C1=O)Cc1cc(c(cc1)OC)O 4.c12c(cc(c(c1C)O)C)CC[C@H](O2)c1c(cc2c(c1)OCO2)O 5.Cc1c(c2c(c(c1O)OC)OC[C@@H](C2=O)Cc1ccc(cc1)O)O 6.c12c(cc(c(c1O)OC)O)OC[C@@H](C2=O)Cc1cc(c(cc1)O)OC 7.c12c(c(c3c(c2)OCO3)O)C(=O)C[C@H](O1)c1c(c(ccc1)O)O 8.c12c(c(c(c(c2O)C)OC)OC)OC[C@H](C1=O)Cc1cc(c(cc1)O)O 9.c12c(c(c(cc2O)OC)O)OC[C@@H](C1=O)Cc1cc(c(cc1)O)O 10.c12c(c(c(cc2O)OC)OC)O[C@@H]([C@H](C1=O)O)c1cc(c(cc1)O)O 11.Cc1c(c2c(c(c1O)OC)OC[C@@H](C2=O)Cc1ccc(cc1O)OC)O 12.c12c(c(c(cc2O)OC)OC)O[C@@H](CC1=O)c1c(ccc(c1)O)O 13.COc1c(cc2c(c1O)C(=O)C[C@H](O2)c1cc(ccc1O)O)O 14.COc1cc2c(cc1O)C[NH+]1Cc3c(cc(c(c3O)OC)OC)[C@H]2C1 15.c12c(c(c3c(c1O)OCO3)OC)O[C@@H]([C@H](C2=O)O)c1cc(cc(c1)O)OC 16.COc1c(cc2c(c1O)C(=O)C[C@@H](O2)c1ccc(c(c1)O)O)O 17.c12c(C[C@@H]3N(C1=O)CCc1c3cc(c(c1)OC)O)cc(c(c2O)OC)O 18.Cc1c(c(c(c2c1occ(c2=O)Cc1ccc2c(c1)OCO2)O)C=O)O 19.c12c(cc(c(c1)CCCc1c(c(c(c(c1)C)O)C)O)O)OCO2 20.c12c(c(c(c(c2)OC)OC)O)C(=O)C[C@@H](O1)c1c(ccc(c1)O)O 21.Cc1c(c2c(c(c1O)OC)OC[C@@H](C2=O)Cc1ccc(cc1)OC)O 22.c12c(c(c(c(c1O)OC)OC)OC)O[C@@H](CC2=O)c1ccc(cc1)O 23.c12c(c(c(c(c1O)OC)OC)OC)OC[C@H](C2=O)Cc1ccc(cc1)O 24.c12c(c(cc(c1C)O)C)CC[C@H](O2)c1c(cc2c(c1)OCO2)O 25.c12c(c(c(c(c2)OC)OC)O)C(=O)C[C@H](O1)c1cc(c(cc1)OC)O 26.Cc1c(c(c2c(c1O)C(=O)C[C@@H](O2)c1ccc(c(c1)O)O)C)O 27.COc1cc2c(cc1O)C[NH+]1Cc3c(cc(c(c3O)OC)OC)[C@@H]2C1 28.Cc1c(c(c2c(c1O)C(=O)C[C@H](O2)c1ccc(c(c1)O)O)C)O 29.[C@]12(c3c(C1)cc(c(c3)OC)O)C(=O)c1c(OC2)cc(cc1O)O 30.c1([C@@H]2C(=O)c3c(OC2)cc(cc3O)O)c(c(c(cc1)O)OC)OC 31.[C@]12(c3c(C1)cc(c(c3)O)OC)C(=O)c1c(OC2)cc(cc1O)O 32.C1(=O)c2c(OC[C@@H]1c1cc(c(cc1)OC)O)cc(cc2O)O 33.C1(=O)c2c(OC[C@H]1c1cc(c(cc1)OC)O)cc(cc2O)O 34.c12C(=O)[C@@H](c3c(c(c(cc3)OC)O)OC)COc1cc(cc2O)O 35.[C@@]12(c3c(C1)ccc(c3O)OC)C(=O)c1c(OC2)cc(cc1O)OC 36.[C@]12(c3c(C1)cc(c(c3)OC)OC)C(=O)c1c(OC2)cc(cc1O)O 37.c12C(=O)[C@@H](c3c(cc(cc3)O)OC)COc1cc(cc2O)OC 38.c12[C@@H](Cc3c(cc(cc3O)O)OC)COc1cc(cc2)O 39.COc1ccc(cc1OC)CC(=O)c1c(cc(cc1O)O)O 40.[C@]12(c3c(C1)cc(c(c3)OC)O)C(=O)c1c(OC2)cc(cc1O)OC 41.c12c(OC[C@H](C2)c2c(cc(cc2)OC)O)cc(cc1OC)O 42.c1cc2c(cc1CC(=O)c1c(cc(cc1O)O)O)OCCCO2 43.c12c(cc(cc1OC)OC)OC[C@H](C2)c1c(cc(cc1)O)O 44.c12c(C(=O)C[C@H](O1)c1c(c(ccc1)O)O)c(cc(c2)OC)O 45.C/C(=C\Cc1c(cc2c(c1OC)C[C@@H](CO2)c1ccc(cc1O)O)O)C 46.COC(=O)c1ccc(o1)CC(=O)c1c(cc(cc1O)O)O 47.c1(c(cc(cc1O)O)OC)C(=O)CCc1cc2c(cc1)OCO2 48.c12C(=O)[C@H](Cc3ccc(cc3)O)COc1cc(c(c2O)OC)O 49.c12c(OC[C@@H](C1=O)Cc1cc(c(cc1)O)O)cc(cc2OC)O 50.c12c(OC[C@@H](C1=O)Cc1cc(c(cc1)OC)O)cc(cc2O)O 51.c12c(c(c(cc2O)OC)O)OC[C@@H](C1=O)Cc1ccc(cc1)O 52.c12C(=O)[C@@H](Cc3ccc(cc3)O)COc1cc(c(c2O)OC)O 53.c12c(cc(c(c1)OC)CCCc1c(cc(cc1)O)O)OCO2 54.c12c(cc(c(c1)CCCc1c(c(c(cc1)O)C)O)OC)OCO2 55.COc1c(ccc2c1OC[C@@H](C2)Cc1ccc(cc1)O)O 56.c1(c(cc(cc1OC)O)OC)CCC(=O)c1ccc(cc1)O 57.c1(c(c(C[C@H]2C(=O)OC[C@@H]2Cc2cc(c(cc2)O)OC)ccc1O)O)OC 58.Cc1c(cc(c2c1O[C@H](CC2)c1ccc(cc1)O)O)OC 59.c12C(=O)[C@@H]([C@H](Oc1cc(cc2O)O)c1ccc(cc1)O)C 60.c1(c(cc(cc1)O)O)C(=O)CCc1cc(c(cc1)O)OC 61.c12c(C[C@@H](CO2)Cc2ccc(cc2)O)ccc(c1OC)O 62.c12c(c(cc(c1C)OC)O)CC[C@H](O2)c1ccc(cc1)O 63.c12c(O[C@@H](CC2)c2ccc(cc2)O)cc(cc1OC)O 64.c1(c(cc(cc1OC)CC=C)C/C=C/Oc1cc(c(cc1)O)OC)O 65.c12c(c(cc(c1C)O)OC)CC[C@@H](O2)c1ccc(cc1)O 66.COc1cc(ccc1O)C[C@]1(COc2cc(ccc2[C@H]1O)O)O 67.COc1cc(ccc1O)C[C@]1(COc2cc(ccc2[C@@H]1O)O)O 68.COc1ccc(cc1)OCC(=O)c1c(cc(cc1O)O)O 69.c1(c(c(c(c(c1)O)OC)OC)OC)[C@@H](c1ccc(cc1)O)C=C 70.c1(c(c(c(c(c1)O)OC)OC)OC)[C@H](c1ccc(cc1)O)C=C 71.c1(c(c(c(cc1O)OC)OC)OC)C(=O)/C=C/c1cc(c(cc1)O)O 72.c12c(cc(c(c2)O)OC)OC[C@@H](C1)Cc1ccc(cc1)O 73.c1(c(c(c(cc1O)OC)C)OC)C(=O)CCc1ccc(cc1)O 74.c12c(cc(cc1OC)O)OC[C@@H](C2)Cc1ccc(cc1)O 75.c12c(c(cc(c2)O)OC)C[C@@H]([C@H](O1)c1ccc(cc1)O)O 76.c12C(=O)[C@H]([C@H](Oc1cc(cc2O)O)c1ccc(cc1)O)C 77.c1(c(cc(cc1O)O)OC)CCC(=O)c1ccc(cc1)O 78.c1(c(C(=O)CCc2ccc(cc2)O)ccc(c1OC)O)O 79.COc1ccc(cc1O)[C@H]1CCc2ccc(cc2O1)O 80.c1(c(c(cc(c1OC)O)C/C=C\c1c(cccc1)O)OC)OC 81.[C@H]1(c2c(cc(cc2)O)OC)[C@@H](c2c(OC1)cc(cc2)O)O 82.COc1cc2c(cc1O)C[C@@H](CO2)Cc1ccc(cc1)O 83.[C@H]1(c2c(cc(cc2)O)O)[C@H](Oc2c(O1)cc(cc2)C#CC)C 84.c1([C@H](c2cc(ccc2)O)C=C)c(cc(c(c1)O)OC)OC 85.c12c(c(cc(c2)O)OC)OC[C@@H](C1)Cc1ccc(cc1)O 86.[C@H]1(c2c(cc(cc2)O)O)[C@@H](Oc2c(O1)cc(cc2)C#CC)C 87.c1cc(ccc1CCC(=O)c1c(cc(cc1O)O)O)O 88.c12C(=O)[C@H](Cc3cc(c(cc3)O)O)COc1cccc2O 89.c1(c(cc(cc1)O)OC)C[C@H](Cc1cc(c(cc1)O)OC)O 90.COc1ccccc1CC(=O)c1c(cc(cc1O)O)O 91.COc1ccc(c(c1)O)[C@@H]1Cc2ccc(cc2OC1)O 92.COc1ccc(cc1)CCC(=O)c1c(cc(cc1O)OC)O 93.COc1cc(ccc1O)C[C@@H]1CO[C@@H]([C@@H]1CO)c1ccc(c(c1)O)O 94.COc1ccc(cc1O)/C=C/C(=O)c1c(cc(cc1OC)OC)O 95.COc1ccc(c(c1)O)[C@H]1Cc2ccc(cc2OC1)O 96.COc1cc(c(c(c1)OC)C(=O)/C=C/c1ccc(c(c1)OC)O)O 97.C[NH+]1CCc2cc(c(cc2[C@@H]1CCc1ccc(c(c1)OC)O)O)OC 98.C[NH+]1CCc2cc(c(cc2[C@H]1CCc1ccc(c(c1)OC)O)O)OC 99.COc1cc(ccc1O)C[C@H]1CO[C@@H]([C@@H]1CO)c1ccc(c(c1)O)O 100.COc1cc(c(c(c1OC)O)C(=O)CCc1ccccc1)O 101.COc1cc(ccc1O)C[C@H]1COC(=O)[C@]1(Cc1ccc(c(c1)OC)O)O 102.[C@H]1(c2cc(c(c(c2)O)OC)O)[C@@H](Cc2c(O1)cc(cc2O)O)O 103.c12c(O[C@H](CC1=O)c1cc(c(c(c1)OC)O)OC)cc(cc2O)O 104.COc1c(cc(cc1O)[C@H]1[C@H](Cc2c(cc(cc2O1)O)O)O)O 105.COc1c2cc(ccc2oc1c1cc(c(c(c1)O)OC)O)O 106.COc1cc(ccc1O)[C@H]1[C@@H](Cc2c(cc(cc2O1)O)O)O 107.c12c3c(cc(c1C[C@H]([C@H](O2)c1cc(c(cc1)O)O)O)O)O[C@H](C[C@@H]3C)O 108.c12c(O[C@@H]([C@@H](C2)O)c2cc(c(cc2)O)OC)cc(cc1OC)O 109.[C@@H]1(c2cc(c(c(c2)O)OC)O)[C@H](Cc2c(O1)cc(cc2O)O)O 110.c12c(c(cc(c2)O)O)C[C@@H]([C@H](O1)c1cc(c(cc1)O)OC)O 111.[C@@H]1(c2cc(c(c(c2)O)OC)O)[C@@H](Cc2c(O1)cc(cc2O)O)O 112.c12c(c(cc(c2)O)O)C[C@H]([C@H](O1)c1cc(c(cc1)O)OC)O 113.c12c3c(cc(c1C[C@H]([C@H](O2)c1cc(c(cc1)O)O)O)O)O[C@@H](C[C@H]3C)O 114.c12c(O[C@@H](CC1=O)c1cc(c(c(c1)O)O)OC)cc(cc2O)O 115.c12c([C@@](O[C@@H]3[C@@H]1Oc1c(C3)c(cc(c1)O)O)(C)C)c(c(c(c2)O)OC)O 116.c12c(c(c(cc1O[C@@H](CC2=O)c1cc(cc(c1)O)O)O)C)O 117.O1c2c(C[C@@H]([C@@H]1c1cc(cc(c1)O)O)O)c(cc(c2)O)O 118.c12c(C(=O)[C@@H]([C@@H](O1)c1cc(c(c(c1)O)OC)O)O)c(cc(c2)O)O 119.[C@@H]1(c2cc(c(cc2)OC)OC)[C@@H](Cc2c(O1)cc(cc2O)O)O 120.c1(cc(c(c(c1)O)OC)O)CCc1cc(ccc1)O 121. COc1c(cccc1O)CCc1cc(cc(c1)O)O122. COc1ccc(cc1O)[C@@H]1[C@@H](C(=O)c2c(cc(cc2O1)OC)O)O 123.[C@@H]1(c2cc(c(cc2)OC)O)[C@H](Cc2c(O1)cc(cc2O)OC)O 124.c1(c(c(cc(c1)O)C)C(=O)O)Oc1c(cc(cc1C)O)O 125.c1(cc(c(c(c1)O)OC)O)/C=C\c1cc(cc(c1)O)O 126.c12c(OCO2)cc(cc1OC)CCc1c(ccc(c1)O)O 127.c12c(C(=O)C[C@H](O1)c1cc(c(c(c1)O)OC)O)ccc(c2)OC 128.COc1cc(ccc1O)[C@@H]1[C@@H](c2cc(cc(c2O1)O)CCCO)CO 129.[C@@H]1([C@@H](c2c(O1)c(cc(c2)C=O)O)CO)c1cc(c(cc1)O)OC 130.Cc1cc(c(c(c1)O)Oc1cc(cc(c1O)O)C)O 131.c1cc(c(cc1[C@H]1CCc2c(cc(cc2O1)O)O)O)O 132.COc1ccc(cc1O)[C@@H]1[C@H](C(=O)c2c(cc(cc2O1)O)O)O 133.c1(c(c(ccc1[C@H]1Cc2c(OC1)cc(cc2)O)O)O)OC 134.c12c(c(c(cc2)O)OC)OC[C@@H]([C@H]1O)c1c(cc(cc1)O)OC 135.COc1c(ccc(c1OC)O)[C@@H]1Cc2ccc(cc2OC1)O 136.COc1ccc(cc1O)C[C@H]1C[NH2+]Cc2c1ccc(c2O)OC 137.c12c(C=C(CO2)c2c(cc(cc2)OC)O)ccc(c1OC)O 138.C[NH+]1CCc2cc3c(c(c2[C@@H]1c1ccc(cc1O)O)OC)OCO3 139.[C@@H]1(c2c(c(c(cc2)O)OC)OC)C(=O)c2c(OC1)cc(cc2)O 140.c1(c(c(c(cc1)O)OC)OC)[C@H]1Cc2c(OC1)cc(cc2)O 141.COc1ccc(c(c1OC)O)[C@H]1Cc2ccc(cc2OC1)O 142.c1(c(c(ccc1[C@@H]1Cc2c(OC1)cc(c(c2)O)O)OC)O)OC 143.c1(c(c(c(cc1)OC)O)OC)[C@H]1Cc2c(OC1)cc(c(c2)O)O 144.COc1ccc(c(c1OC)O)[C@@H]1Cc2ccc(cc2OC1)O 145.c1([C@@H]2Cc3c(OC2)c(c(cc3)O)OC)c(c(c(cc1)OC)O)O 146.c12c(cc(c(c1)[C@](C=C)(C)C)O)OC[C@H](C2)c1c(cc(cc1)O)OC 147.COc1c(cc2c(c1O)C(=O)C[C@@H](O2)c1ccc(cc1)O)O 148.COc1cc(c(cc1OC)O)[C@H]1Cc2ccc(cc2OC1)O 149.c1([C@H]2Cc3c(OC2)c(c(cc3)O)O)c(c(c(cc1)OC)O)O 150.c1([C@H]2Cc3c(OC2)cc(cc3)O)c(cc(c(c1)OC)O)O 151.c12c(C[C@H](CO2)c2c(cc(cc2)OC)O)ccc(c1OC)O 152.Cc1c(ccc2c1O[C@H](CC2)c1ccc(c(c1)O)OC)O 153.c1([C@@H]2Cc3c(OC2)c(c(cc3)O)C=O)c(c(c(cc1)OC)O)OC 154.c1(c(c(c(cc1)OC)O)OC)[C@@H]lCc2c(OC1)c(c(cc2)O)O 155.c12c(c(ccc1CC[C@H](O2)c1c(cc(cc1)O)O)OC)CCO 156.c12OC[C@@H](c3c(c(c(cc3)OC)O)OC)Cc2ccc(c1O)O 157.COc1ccc(cc1O)C[C@@H]1C[NH2+]Cc2c1ccc(c2O)OC 158.c1(c(c(c(cc1)O)OC)OC)[C@H]1Oc2c(CC1)ccc(c2)O 159.COc1ccc(c(c1O)OC)[C@H]1Cc2ccc(cc2OC1)O 160.[C@@H]1(c2c(cc(c(c2)OC)O)O)C(=O)c2c(OC1)cc(cc2)O 161.c1([C@@H]2C(=O)c3c(OC2)cc(cc3)O)c(cc(c(c1)O)OC)OC 162.c12c(c(c(c(c1)O)OC)OC)CCN[C@@H]2Cc1ccc(cc1)O 163.c12c(OC[C@@H](c3c(cc(cc3)OC)O)C1)cc(c(c2)OC)O 164.Cc1c(cc2c(c1O)CC[C@@H](O2)c1ccc(cc1)O)OC 165.C[NH+]1Cc2c(ccc(c2O)OC)[C@@H](C1)Cc1cccc(c1OC)O 166.Cc1c(ccc2c1O[C@@H](CC2)c1ccc(c(c1)O)OC)O 167.COc1cc(ccc1O)[C@@H]1CCc2cc(c(cc2O1)O)OC 168.Cc1c(ccc2c1O[C@H](CC2)c1ccc(c(c1)OC)O)O 169.COc1cc(ccc1O)[C@H]1CCc2cc(c(cc2O1)O)OC 170.C[NH+]1CCc2cc3c(c(c2[C@H]1c1ccc(cc1O)O)OC)OCO3 171.C[NH+]1Cc2c(ccc(c2O)OC)[C@@H](C1)Cc1cccc(c1O)OC 172.C[NH+]1Cc2c(ccc(c2O)OC)[C@H](C1)Cc1cccc(c1OC)O 173.COc1cc2c(cc1O)[C@H]1Cc3cc(c(cc3C[NH+]1CC2)OC)O 174.CCCc1cc(c(cc1O)O)C(=O)Cc1ccc2c(c1)OCO2 175.COc1ccc2c(c1OC)C(=O)O[C@@H]2Nc1ccc(cc1)O 176.c1ccc2c(c1)c(=O)n(cn2)CCCC(=O)Nc1ccccc1C(=O)N 177.COc1cc2c(cc1OC)ncn(c2=O)CCC(=O)Nc1ccc(cc1)C(=O)N 178.c1ccc2c(c1)c(=O)n(cn2)CC(=O)Nc1ccccc1C(=O)N 179.c12c([C@@H](c3cc(c(cc3)O)OC)CC(=O)O2)c(cc2c1C[C@@H]([C@H](O2)c1cc(c(c(c1)O)OC)O)O)O180.c12c(O[C@H]([C@@H]1CO)c1cc(c(cc1)O)OC)c(ccc2[C@@H]1Oc2c(C(=O)C1)c(cc(c2)O)O)O181.COc1cc(ccc1O)[C@@H]1[C@@H](Oc2ccc(cc2O1)[C@H]1[C@H](C(=O)c2c(cc(cc2O1)O)O)O)CO182. c1ccc2c(c1)c(=O)n(cn2)CC(=O)NCC(=O)Nc1ccccc1C(=O)N 183.c12[C@H](c3cc(c(cc3)O)OC)CC(=O)Oc1cc(cc2/C=C/c1cc(c(cc1)O)OC)O 184.COc1cc(ccc1O)CC[C@H]([C@@H](Cc1cccc(c1)O)C(=O)CCc1cc(c(c(c1)OC)O)O)O185.C[C@]12C[C@H](C[C@](C1)(C)C)[NH+](C2)Cc1c(ccc2c1oc(c(c2=O)c1nc2ccccc2s1)N)O186.[C@@H]1([C@H](c2cc(c(cc2)OC)OC)C=CC[C@@H]1c1cc(c(cc1)O)OC)C(=O)/C=C(/C=C/c1cc(c(cc1)O)OC)O187. COc1cc2c(cc1OC)c1cc(nc(=O)n1CC2)Nc1ccc(cc1)C(=O)[O−] 188.COc1cc(cc(c1OC)OC)NC(=O)C[C@H]1C(=O)Nc2ccccc2C(=O)N1 189.COCCC[n+]1c(N)c(cc2c1nc1ccccn1c2=O)C(=O)NCCc1ccc(c(c1)OC)OC 190.COc1cc(ccc1O)[C@H]1[C@H](c2c(ccc(c2O1)O)[C@H]1[C@@H](C(=O)c2c(cc(cc2O1)O)O)O)CO191.CCc1cc2c(=O)c(c(oc2c(c1O)C[NH+]1C[C@@H]2C[C@H](C1)c1cccc(=O)n1C2)C)c1nc2ccccc2n1C192. c1cc(ccc1C(=O)N)NC(=O)COc1ccc2c(c1)c(=O)n1c(n2)CCC1 193.CCc1nc2cc(c(cc2c(=O)n1CCNC(=O)c1cccnc1)OC)OC 194.COCCCNC(=O)c1cc2c(nc3ccccn3c2=O)[n+](c1N)CCc1ccc(c(c1)OC)OC 195.C[C@@H](C)[n+]1c(N)c(cc2c1nc1ccccn1c2=O)C(=O)NCc1ccc(cc1)OC 196.C[C@@H](C)[n+]1c(N)c(cc2c1nc1ccccn1c2=O)C(=O)NCCc1ccc(cc1)OC 197.CC[n+]1c(N)c(cc2c1nc1ccccn1c2=O)C(=O)NCc1ccc2c(c1)OCO2 198.COc1cc2c(cc1OC)ncn(c2=O)CCC(=O)Nc1ccc(cc1)C(=O)OC 199.c1ccc2c(c1)c(=O)n(cn2)CCC(=O)Nc1ccc2c(c1)COC2=O 200.COc1cc2c(cc1OC)c1cc(nc(=O)n1CC2)Nc1ccc(cc1)C(=O)OC 201.COc1cc2c(cc1O)[C@H]1c3ccc(cc3OC[C@]1(C2)O)O 202.c12c3c(CCc1cc(c(c2)O)O)cc(cc3OC)O 203.COc1cc2c(cc1O)[C@@H]1c3ccc(cc3OC[C@@]1(C2)O)O 204.c12c(c(c(cc2OC)O)O)CCc2c1ccc(c2)O 205.COc1ccc(cc1O)[C@@H]1C[NH2+]Cc2c1ccc(c2O)OC 206. COc1c(cc(cc1O)O)O 207.COc1ccc(cc1O)[C@H]1C[NH2+]Cc2c1ccc(c2O)OC 208.COc1ccc2c(c1O)CNC[C@@H]2c1ccc(c(c1)O)O 209.COc1ccc2c(c1O)CNC[C@H]2c1ccc(c(c1)O)O 210.C[C@]1(CC(=O)c2c(cc(cc2O1)O)O)C 211. c12c3c(CCc1cc(c(c2OC)O)O)cc(cc3)O212. COc1cc2c(cc1O)[C@H]1C[NH+](C2)Cc2c1cc(c(c2)OC)O 213.COc1ccc2c(c1O)C[NH+]1Cc3c(ccc(c3O)OC)[C@@H]2C1 214.COc1cc(ccc1O)[C@@H]1C[NH2+]Cc2c1cc(c(c2)O)OC 215.c1[nH]c(=O)c2c([nH]nc2n1)C(=O)[O−] 216.COc1ccc(cc1OC)[C@H]1c2cc(c(cc2C[C@H](C(=O)[O−])[NH2+]1)O)O 217.COc1cc(ccc1O)[C@H]1C[NH2+]Cc2c1cc(c(c2)O)OC 218.Cc1cc2c(cc1/N=C/N(C)C)nc1c(n2)c(=O)n(c(=O)n1C)C 219.Cc1cc(nc2c1c1c(o2)c(=O)n(cn1)CC(=O)N)C 220.COc1ccc(cc1OC)[C@@H]1c2cc(c(cc2C[C@H](C(=O)[O−])[NH2+]1)O)O 221.COc1ccc(cc1OC)[C@H]1c2cc(c(cc2C[C@@H](C(=O)[O−])[NH2+]1)O)O 222.Cc1cc(nc2c1c1c(o2)c(=O)n(cn1)C)C 223.COc1cc(ccc1O)[C@@H]1c2cc(c(cc2C[C@@H]2[C@@H]1COC2=O)OC)O 224.COc1cc2c(cc1O)C[NH+]1Cc3cc(c(cc3[C@H]2C1)OC)O 225.c12c3c4COc1c(cc(c2CCc3cc(c4)O)O)OC 226.c12c(oc3c(c1=O)c(cc(c3)O)C)c(c(cc2O)OC)C1 227.c12c3c4OCc1c(c(cc2CCc3cc(c4)O)OC)O 228.Cc1cc(cc2c1c(=O)c1c(cc(cc1o2)O)O)O 229.COc1c2c3c(c(c1OC)O)COc1c3c(cc(c1)O)CC2 230.c12c(c(=O)c3c(o2)cc(cc3O)O)ccc(c1OC)OC 231.COc1c(ccc2c1c(=O)c1c(cc(cc1o2)O)O)O 232.COc1cc2c(cc1OC)OCc1c2c(=O)c2c(cc(cc2o1)O)O 233.c12c(c3c(cc1C[C@@](CC2=O)(O)C)cc(cc3O)OC)O 234.c12c3c4O[C@@H](c1c(c(cc2CCc3cc(c4)O)O)OC)O 235.c12c3c(cc(c(c3)OC)O)CCc1cc(c(c2OC)O)O 236.c12c(C(=O)c3c(C1=O)c(cc(c3OC)CO)O)cc(c(c2OC)OC)O 237.c12c(c(=O)c3c(n1C)c(c(cc3)O)OC)c(cc(c2OC)OC)O 238.c12c3c4cc(cc3CCc2c(c(c(c1OC4)OC)O)OC)O 239.c12c(n(c3c(c1=O)ccc(c3OC)OC)C)cc(c(c2O)OC)O 240.c12c(oc3c(c1=O)cc(c(c3)O)OC)cc(cc2OC)O 241.Cc1cc(cc(c1C(=O)c1c(cc(cc1O)OC)O)OC)O 242.c12c(oc3c(c1=O)c(cc(c3)OC)O)cc(c(c2O)OC)OC 243.Cc1cc(cc2c1c(=O)c1c(cc(cc1o2)OC)O)O 244.COc1cc(c2c(c1)oc1ccc(c(c1c2=O)OC)O)O 245.Cn1c2cc(c(c(c2c(=O)c2c1c(ccc2)O)O)OC)OC 246.Cc1cc2c(c(c1)O)C(=O)c1c(cc(cc1O)O)C2=O 247.Cc1cc2c(c(c1)O)C(=O)c1c(cccc1O)C2

TABLE 2 No. SMILES structures 1.CCC(=O)NCC(C)(C)COC1=C2C(N)=NS(=O)(=O)NC2=CC=C1 2.COC1=C(O)C=C2C(CC22COC3=CC(O)=CC(O)=C3C2=O)=C1 3.COC1=C(O)C=C(CC2COC3=CC(O)=CC(O)=C3C2=O)C=C1 4.COC1=CC(O)=C2C(=O)CC(OC2=C1)C1=CC(O)=CC(O)=C1 5.COC1=C(O)C=C(C=C1)[C@@H]1CC(=O)C2=C(O)C=C(O)C=C2O1 6.COC1=C(O)C=C(C=C1)C1CC(=O)C2=C(O)C=C(O)C=C2O1 7.COc1ccc(cc1O)[C@@H]1CC(=O)c2c(cc(cc2O1)O)O 8.COC1=C(O)C=C(C=C1)C1OC2=CC(O)=CC(O)=C2CC1O 9.COc1ccc(cc1O)[C@@H]1CCc2c(cc(cc2O1)O)O 10.COC1=C(O)C=CC(=C1)C1OC2=CC(O)=CC(O)=C2CC1O 11.COC1=CC=C(C=C1O)[C@H]1OC2=C(C[C@H]1O)C(O)=CC(O)=C2 12.CC1=C(C)C2=C(NC(=O)N=C2N)S1 13.COC1=CC(=CC=C1O)[C@H]1OC2=C(C[C@H]1O)C(O)=CC(O)=C2 14.COC1=C(O)C=CC(=C1)[C@H]1OC2=C(C[C@@H]1O)C(O)=CC(O)=C2 15.COC1=C(O)C2=C(C=C1)C1OC3=CC(O)=CC=C3C1CO2 16.COC1=C(O)C2=C(OCC3C2OC2=CC4=C(OCO4)C=C32)C=C1O 17.COC1=CC(O)=C2C(=O)C(COC2=C1)C1=C(OC)C=C(O)C=C1 18.COC1=CC=C(C=C1O)C1CC(=O)C2=C(O1)C=C(O)C=C2O 19.COC1=CC2=C(OCO2)C=C1C1COC2=CC(O)=CC(O)=C2C1=O 20.COc1cccc(NC(=O)Cn2c3sc(C)cc3c(N)nc2=O)c1 21.COC1=CC=C(C=C1)C1CC(=O)C2=C(O1)C=C(O)C=C2O 22.COC1=C(C=CC(O)=C1)C1COC2=CC(O)=CC(OC)=C2C1=O 23.COC1=CC(O)=C(C=C1)C1COC2=CC(O)=CC(O)=C2C1=O 24.COc1ccc(cc1O)[C@@H]1CCc2c(cccc2O1)O 25.COC1=C(OC)C(O)=C(C=C1)C1COC2=C(C1)C=CC(O)=C2 26.COC1=C(O)C(OC)=C(C=C1)C1COC2=CC(O)=CC=C2C1 27. OC1=CC(O)=CC(O)=C1 28.COC1=C(O)C2=C(C(=O)C(CC3=CC=C(O)C=C3)CO2)C(O)=C1OC 29.COC1=CC=C(C=C1O)C1CCC2=C(O1)C=C(O)C=C2 30.COC1=C(OC)C2=C(C(O)=C1)C(=O)C1=C(N2C)C(O)=CC=C1 31.COC1=CC=C(C2COC3=CC(O)=CC=C3C2)C(OC)=C1O 32.COC1=C(O)C=C(CC2(O)OC3=C(C=CC(O)=C3)C2=O)C=C1 33.COc1ccc(cc1O)[C@@H]1CCc2ccc(cc2O1)O 34.COc1ccc(CCC(=O)c2c(cc(cc2O)O)O)cc1O 35.COC1=C(O)C=CC(=C1)C1OC2=CC(O)=CC(O)=C2C(=O)C1O 36.COC1=CC2=C(C=C1O)C1COC3=CC(O)=CC=C3C1O2 37.COC1=CC2=C(C=C1O)C1COC3=C(C=CC(O)=C3)C1O2 38.Nc1nc(=S)[nH]c2sc3CCCCc3c12 39.COC1=C(O)C2=C(C=C1)C1OC3=C(C=CC(O)=C3OC)C1CO2 40.COC1=CC(OC)=C(C=C1)C1COC2=CC(O)=CC(O)=C2C1=O 41.COC1=C(O)C=C(\C=C/C2=CC(O)=CC(O)=C2)C=C1O 42.OC1CC(OC2=CC(O)=CC(O)=C12)C1=CC=C(O)C=C1 43.COC1=CC(O)=C(C=C1)C1CC(=O)C2=C(O)C=C(OC)C=C2O1 44.Nc1nc(=S)[nH]c2sc3CCCc3c12 45.COC1=C(OC)C2=C(C(O)=C1)C(=O)C(CC1=CC=C(O)C=C1)CO2 46.COC1=CC(O)=C(C=C1)C1COC2=CC(O)=C(OC)C=C2C1 47.COC1=CC(O)=C2C(=O)CC(OC2=C1)C1=CC(O)=C(OC)C=C1 48.COc1cccc(C(N)=N)c1NS(N)(=O)=O 49. Cc1cc2c(N)nc(=O)n(CC(=O)Nc3ccccc3)c2s150. COC1=C(C=CC(O)=C1)C1COC2=CC(O)=CC(O)=C2C1=O 51.COC1=C(O)C2=C(C(O)=C1)C(=O)C(CC1=CC=C(O)C=C1)CO2 52.C[C@]12c3ccc(c(c3OC[C@@]2(Cc2cc(c(cc12)OC)O)O)O)O 53.COC1=C(O)C(O)=C(C)C=C1O 54. COC(=O)C1=C(O)C=C(O)C=C1O 55.CC1CCc2c(C1)sc1[nH]c(=S)nc(N)c21 56.COC1=C2C(=O)C(CC3=CC(O)=C(O)C=C3)COC2=CC(O)=C1 57.COC1=CC(O)=C2CC(O)C(OC2=C1)C1=CC(O)=C(OC)C=C1 58.Cc1c(sc2nc[nH]c(=O)c12)C(=O)Nc1cc(C)cc(C)c1 59.COC1=CC=C(C=C1O)C1COC2=C(C=CC(O)=C2)C1=O 60.COC1=C(O)C=C(C=C1)C1COC2=C(C=CC(O)=C2)C1=O 61.COC1=C(O)C2=C(N(C)C3=C(C=CC=C3O)C2=O)C(OC)=C1OC 62.COC1=C(OC)C2=C(C3=C1OCO3)C(=O)C1=C(C(O)=C(C)C=C1O)C2=O 63.COC1=C(O)C=C2C(CC3C4=CC(O)=C(OC)C=C4CC[N+]23 C)=C1 64.COC1=CC2=C(C(=O)C3=C(C(O)=CC(C)=C3O)C2=O)C(OC)=C1OC 65.Nc1nc(=S)[nH]c2sc3CN(Cc4ccccc4)CCc3c12 66. CC1=CC(O)=CC(O)=C1 67.Cc1cc(C)c(NC2=NS(=O)(=O)c3ccccc23)c(C)c1 68.COC1=CC2=C(C=C1OC)C1C(CO2)OC2=CC(O)=CC=C2C1=O 69.COC1=C(O)C=C(O)C2=C1N(C)C1=C(C=CC=C1O)C2=O 70.COC1=CC(O)=C(C=C1)C1COC2=CC(O)=CC=C2C1O 71. NC(=N)c1cc(F)ccc1NS(N)(=O)=O72. COc1ccc(NC(=O)Cn2c3sc(C)cc3c(N)nc2=O)cc1 73.COC1=C(O)C=C(C=C1)C1(COC(C)=O)COC2=CC(O)=CC(O)=C2C1=O 74.COC1=C2OC3=C(C=CC(O)=C3OC)C2=CC(O)=C1OC 75.COC1=CC=C(C2COC3=CC(O)=CC=C3C2)C(O)=C1 76.COC1=CC(O)=C(OC2=CC(C)=CC(O)=C2)C(C)=C1 77.CCCOC1=C(C=C(C=C1)S(N)(=O)=O)C1=NC2=C(N(C)N=C2CCC)C(=O)N1 78.COC1=CC(=CC=C1O)C1CC(=O)C2=C(O)C=C(O)C=C2O1 79.COC1=CC(=CC=C1O)C1OC2=CC=C(C=C2OC1CO)C1OC2=CC(O)=CC(O)=C2C(=O)C1O 80.NC(=N)c1c(F)cccc1NS(N)(=O)=O 81.COC1=C(O)C=CC(=C1)C1OCC2(O)C1COC2C1=CC(OC)=C(O)C=C1 82.C[C@]12c3ccc(c(c3OC[C@@]2(Cc2cc(c(cc12)O)OC)O)O)O 83.COC1=C(O)C=C(C2COC3=C(C2)C=CC(O)=C3)C(OC)=C1OC 84.OC1=CC2=C(C=C1)C1COC3=C(C=CC(O)=C3O)C1O2 85.COC1=C(O)C=CC(=C1)C1OC2=C(O)C=CC(C3OC4=CC(O)=CC(O)=C4C(=O)C3O)=C2C1CO86. COc1ccc(CCC(=O)c2c(cc(cc2O)OCCS(=O)(=O)O)O)cc1[O−] 87.COC1=CC2=C(C(O)=C1)C(=O)C1=C(N2C)C2=C(OCO2)C=C1 88.COC1=C2OCOC2=CC(=C1)C1CC(=O)C2=C(O1)C=C(O)C(OC)=C2O 89.COC1=C(O)C=C(CC2COC3=CC(O)=CC(OC)=C3C2=O)C=C1 90.OC1=CC(O)=C2C(=O)C=COC2=C1 91.COC1=CC2=C(C=C1O)C1=C(O2)C(OC)=C(OC)C(O)=C1 92.COC1=CC2=C(C(O)=C1)C(=O)C1=C(O2)C2=C(O)C=C(O)C3=C2C(C1)C(C)(C)O3 93.CNc1nc(=S)[nH]c2sc3CCCCc3c12 94.COC1=C(O)C=CC(=C1)C1OC2=C(C=C(C=C2O)C2CC(=O)C3=C(O)C=C(O)C=C3O2)C1CO 95.COc1ccccc1NC(=O)Cn1c2sc(C)cc2c(N)nc1=O 96.CC1=CC(O)=C2C(=O)C3=C(O)C=C(O)C=C3CC2=C1 97.OC1=CC=C2C(OC3C4=C(OCC23O)C=C(O)C=C4)=C1 98.OC1C(COC2=C1C=CC(O)=C2)C1=C(O)C=C2OCOC2=C1 99.COC1=CC2=C(C=C1)C1(O)COC3=C(C=CC(O)=C3)C1O2 100.COC1=CC=C(C=C1O)C1OC2=C(C(O)=CC(O)=C2)C(=O)C1O 101.COC1=C(O)C=C2OC3=C(C(O)=C4CCC(C)(C)OC4=C3)C(=O)C2=C1CCC(C)(C)O 102.Nc1c(C#N)c(=O)[nH]c2sc3CCCc3c12 103.OC1=CC=C(C=C1)C1CC(=O)C2=C(O1)C=C(O)C=C2O 104.Cc1cc2c(N)nc(=O)n(CC(=O)Nc3cccc(Cl)c3)c2s1 105.COC1=CC(C=CC(O)=CC(=O)CCC2=CC(OC)=C(O)C=C2)=CC=C1O 106.COC1=CC2=C(C(=O)C [C@H](O2)C2=CC=C(O)C=C2)C(O)=C1 107.COc1ccccc1NC(=O)Cn1c2sc3CCCCCc3c2c(N)nc1=O 108.COC1=CC2=C(C3CCOC3O2)C2=C1C(=O)C1=C(O)C=CC=C1O2 109.CC1(C)C2CCC3(C)OC4=C(C=C(C5CC(=O)C6=C(O)C=C(O)C=C6O5)C(O)=C4)C1C23 110.COC1=C(O)C=CC(=C1)C1=C(O)C(O)=CC2=C1COCC2 111.COC1=C2OC(C(CO)C2=CC(CC2C(CC3=CC=C(O)C(OC)=C3)COC2=O)=C1)C1=CC=C(O)C(OC)=C1112. COC1=CC(=CC=C1O)C1OC2=C(C1CO)C(=CC=C2O)C1CC(=O)C2=C(O1)C=C(O)C=C2O113. COC1=CC(CCC(O)=CC(=O)CCC2=CC(OC)=C(O)C=C2)=CC=C1O 114.COc1cccc2CC(COc12)C(=O)NCCc1nc(N)cc(O)n1 115.COC1=CC2=C(C=C1)C1COC3=C(C=CC(O)=C3O)C1O2 116.CCc1cnc(C)nc1NCCc1nc2sc(C)c(C)c2c(=O)[nH]1 117.COC1=C(CC=C(C)C)C(O)=C(C=C1)C1COC2=CC(O)=CC(OC)=C2C1 118.COC1=CC(OC)=C(C=C1)C1CC(=O)C2=C(OC)C=C(O)C=C2O1 119.NC(=N)c1ccccc1NS(N)(=O)=O 120.COC1=CC2=C(C3C=COC3O2)C2=C1C(=O)C1=C(O)C=CC=C1O2 121.COC1=CC(=CC=C1O)[C@@H]1CC(=O)C2=C(O1)C=C(O)C=C2O 122.OC1CC(OC2=C1C(O)=CC(O)=C2)C1=CC=C(O)C=C1 123.COC1=CC(=CC(O)=C1O)C1OC2=CC(O)=CC(O)=C2C(=O)C1O 124.O[C@H]1CC2=C(O[C@H]1C1=CC=C(O)C(O)=C1)C=C(O)C=C2O 125.COC1=C(OC)C(O)=C(OC)C2=C1OC1=C2C=CC(O)=C1 126.COC1=CC=C(\C=C\C2=CC(O)=C(OC)C(CO)=C2)C=C1O 127.COC1=C(O)C=CC(=C1)C1C2COC3(O)C2C(CC1C3=O)C1CC(=O)C2=C(O)C=C(O)C=C2O1128. COc1ccc(cc1O)[C@@H]1[C@H](C(=O)c2c(cc(cc2O1)O)O)O 129.COc1ccc(cc1O)[C@@H]1CC(=O)c2ccc(cc2O1)O 130.COC1=CC(=CC=C1O)C1OC2=C(OC1CO)C=CC(=C2)C1OC2=C(C(O)=CC(O)=C2)C(=O)C1O131.COC1=C(O)C=CC(=C1)C1OC2=C(OC1CO)C=CC(=C2)C1OC2=CC(O)=CC(O)=C2C(=O)C1O132. COC1=C(O)C=CC(C\C=C\C(=O)CC(=O)\C=C/CC2=CC(OC)=C(O)C=C2)=C1 133.OC1=CC(O)=C2C(=O)CC(OC2=C1)C1=CC=CC=C1O 134.COc1c(C)cc(cc1C)S(=O)(=O)Nc1ccc2NC(=O)C(C)(C)COc2c1 135.OC1=CC=CC(=C1)C(=O)C1=C(O)C=C(O)C=C1O 136.COC1=CC(C2OC3=CC(OC)=CC(O)=C3C(=O)C2O)=C(O)C=C1 137.COC1=CC=C(C=C1)C1CC(=O)C2=C(O)C=C(O)C(C)=C2O1 138.COC1=C(O)C(O)=CC(=C1)C1OC2=CC(O)=CC(O)=C2C(=O)C1O 139.CC1(C)OC2=C(CC1O)C1=C(C(O)=C2)C(=O)C(CO1)C1=C(O)C=C(O)C=C1 140.Cc1cccc(NS(N)(=O)=O)c1C(N)=N 141.COc1cccc(NC(=O)Cn2c3sc4CCCCCc4c3c(N)nc2=O)c1 142.CC1(C)OC2=C(C=C1)C(O)=C(C=C2)C1COC2=C(C1)C=CC(O)=C2 143.OC1CC(OC2=CC(O)=CC(O)=C12)C1=CC=C(O)C(O)=C1 144.COC1=C(O)C=C2OC3=C(C(O)=C4CCC(C)(C)OC4=C3)C(=O)C2=C1CC=C(C)C 145.COC1=C(O)C=CC(=C1)C1C2COC3(O)C2C(CC1C3=O)C1OC2=CC(O)=CC(O)=C2C(=O)C1O146. COC1=CC=C(C=C1)C1OC2=C(C(O)=CC(O)=C2)C(=O)C1O 147.COC1=CC(=CC=C1O)C1OC2=CC=C(C=C2OC1CO)C1CC(=O)C2=C(O)C=C(O)C=C2O1 148.COC1=CC2=C(C(O)=C1CC(O)C(C)=C)C(=O)C1=C(CC=C(C)C)C(OC)=C(O)C=C1O2 149.Cc1ccc(C)c(NS(=O)(=O)c2ccc(NC3=NS(=O)(=O)c4ccccc34)cc2)c1 150.CCOc1c(C)cc(cc1C)S(=O)(=O)Nc1ccc2NC(=O)C(C)(C)COc2c1 151.COC1=C2CC(COC2=C(C=O)C(O)=C1)C1=C(O)C(CC=C(C)C)=C(O)C=C1 152.CCOc1ccccc1C(=O)N1CCC2(CC1)NC(=NO2)c1cccc(Br)c1 153.OC1CC(OC2=CC(O)=CC(O)=C12)C1=CC(O)=C(O)C=C1 154.COC1=C(O)C=C2OCC(CC2=C1)C1=CC=C(O)C=C1 155.COC1=C(O)C=C2OC[C@@H](CC2=C1)C1=CC=C(O)C=C1 156.CC(C)C(=O)C1=C(O)C=C(O)C=C1O 157.O[C@@H]1CC2=C(O[C@@H]1C1=CC=C(O)C=C1)C=C(O)C=C2O 158.OC1CC2=C(OC1C1=CC=C(O)C=C1)C=C(O)C=C2O 159. COC1=C(O)C=C(C=O)C=C1O 160.CN1CCc2c(C1)sc1[nH]c(=S)nc(Nc3ccccc3)c21 161.CC1=CC2=C(C(O)=C1)C(=O)C1=C(O)C=C(O)C=C1C2 162.COC1=CC(=CC(O)=C1OC)C1CCC2=C(O1)C(O)=C(OC)C=C2 163.COc1ccc(cc1O)[C@@H]1CC(=O)c2c(cccc2O1)O 164.COc1c(C)cc(cc1C)S(=O)(=O)Nc1ccc2OCC(C)(C)C(=O)Nc2c1 165.CC(=O)C1=C(O)C=C(O)C=C1O 166.CC(=C)C(O)CC1=C2OC3C(COC4=CC(O)=CC=C34)C2=CC=C1O 167.[H][C@]1(COC2=C(C=CC(O)=C2)C1=O)C1=C(O)C=C2OCOC2=C1 168.COC1=C(O)C=CC2=C1OC(CC2=O)C1=CC=C(O)C=C1 169.COC1=CC(O)=C2C(=O)C(O)C(OC2=C1)C1=CC(O)=C(OC)C=C1 170.OC1CC2=C(O)C=C(O)C=C2OC1C1=CC=C(O)C=C1 171.CCCC1=NN(C)C2=C1NC(=NC2=O)C1=C(OCC)C=CC(=C1)S(=O)(=O)N1CCNCC1 172.CC1=CC(O)=C(C=O)C2=C1C(=O)OC1=C(O2)C=C2OC(C)(C)CC(=O)C2=C1C 173.COC1=C(OC(=O)C(C)C)C=CC(=C1)C1CC(=O)C2=C(O)C=C(O)C=C2O1 174.CCOc1c(C)cc(cc1C)S(=O)(=O)Nc1ccc2OCC(C)(C)C(=O)Nc2c1 175.COc1ccc(cc1C)S(=O)(=O)Nc1ccc2OCC(C)(C)C(=O)Nc2c1 176.CCCC1=C(O)C(=CC=C1O)C1=C(OC)C=C(C)C=C1OC 177.COC1=C(O)C=CC2=C1OC1=CC(O)=CC(O)=C1C2=O 178.OC1=CC(O)=C2C(=O)CC(OC2=C1)C1=CC=C(O)C(O)=C1 179.COC1=C(O)C2=C(OC(CC2=O)C2=CC=CC=C2)C=C1O 180.Cc1cc2c(N)nc(=O)n(Cc3ccc(Cl)cc3Cl)c2s1 181.COC1=C(O)C=C2CC3NCCC4=CC(O)=C(OC)C(C2=C1)=C34 182.OC1=CC=C(CC2COC3=CC(O)=CC(O)=C3C2=O)C=C1 183.COC1=C(O)C=CC(=C1)C1OCC2(OC(C)=O)C1COC2C1=CC(OC)=C(O)C=C1 184.COC1=C(OC)C2=C(C=C1)C(=O)CC(O2)C1=CC=C(O)C=C1 185.OC1=CC(O)=C(C=C1)C1COC2=CC(O)=CC(O)=C2C1=O 186.COc1cc(Nc2ncnc3sc(C(O)=O)c(C)c23)cc(OC)c1OC 187.COC1=C(O)C=CC(CC2COC(=O)C2(O)CC2=CC(OC)=C(O)C=C2)=C1 188.COC1=CC=C(C=C1)C1COC2=C(C)C(O)=CC(O)=C2C1=O 189.COC1=CC2=C(C(O)=C1)C(=O)C1=C(O2)C2=C(OC)C=C(O)C3=C2C(C1)C(C)(C)O3 190.COC1=C(O)C=C2C3CC4=CC(O)=C(O)C=C4[N+]3(C)CCC2=C1 191.COC1=C(O)C=C(O)C2=C1OC(CC2=O)C1=CC=CC=C1 192.COC1=CC2=C(OC3=CC(O)=CC(O)=C3C2=O)C=C1 193.OC1=CC(O)=C(C=C1)C1COC2=C(C1)C=CC(O)=C2 194.OC1=C(O)C=C(C=C1)[C@H]1OCC2C1CO[C@@H]2C1=CC=C2OCOC2=C1 195.CN1C2=C(C(O)=CC(O)=C2)C(=O)C2=C1C(O)=CC=C2 196.COC1=CC(CC2COC(C2CO)C2=CC=C(O)C(OC)=C2)=CC=C1O 197.CC(=O)O[C@H]1C(=O)c2c(cc(cc2O[C@@H]1c1ccc(c(c1)O)OC)O)O 198.COC1=C(O)C(O)=C(C=C1)C1COC2=C(C1)C=CC1=C2C=CC(C)(C)O1 199.COC1=CC(O)=C(C=C1)C1COC2=C(C=CC(O)=C2)C1=O 200.COC1=CC(OC)=C2C(O)=C3C(=O)CC(C)(O)OC3=CC2=C1 201.COc1cc(N)c(cc1OC)C(\N)=N\O 202.COC1=C(O)C=CC2=C1N(C)C1=C(C(O)=CC(O)=C1)C2=O 203.COC1=C(OC(C)=O)C2=C(C(O)=C1)C(=O)C(CC1=CC=C(O)C=C1)CO2 204.COc1ccc(Nc2nc(C)nc3sc4CCCc4c23)cc1O 205.COC1=CC(O)=C2C(=O)[C@@H](O)[C@H](OC2=C1)C1=CC=C(O)C=C1 206.COc1ccc(cc1O)C1Cc2cccc(c2C(=N1)O)O 207.COC1=CC(O)=C2C(=O)CC(OC2=C1)C1=CC=C(O)C=C1 208.N\C(=N\O)c1c(F)cccc1NS(N)(=O)=O 209.COC1=CC(O)=C(C=C1)C1(O)COC2=CC(O)=CC=C2C1=O 210.COC1=C(C)C(O)=C(C(=O)CCC2=CC=CC=C2)C(O)=C1C 211.N\C(=N\O)c1ccccc1NS(N)(=O)=O 212. NC(=O)Cn1c2sc3CCCc3c2c(N)nc1=O 213.COC1=CC2=C(C(O)=C1CC=C(C)C)C(=O)C1=C(CC(O)C(C)=C)C(OC)=C(OC)C=C1O2 214.COC1=C2C(=O)C3=C(OC2=C(O)C=C1O)C(O)=CC=C3 215.Cc1ccc(cc1)S(=O)(=O)\N=C(/Nc1ccc2[nH]c(=O)[nH]c2c1)c1ccccc1 216.COC1=CC2=C(C=C1OC)C(=O)C1=C(C(O)=CC(C)=C1O)C2=O 217.CC(=C)Cn1c2sc(C)cc2c(N)nc1=O 218.COC1=C(O)C2=C(C=C1O)C(=O)C1=C(C(O)=CC=C1O)C2=O 219.NC(=O)Cn1c2sc3CCCCc3c2c(N)nc1=O 220.COC1=C(O)C=CC(=C1)C1OC2=C(C=C(C=C2O)C2OC3=CC(O)=CC(O)=C3C(=O)C2O)C1CO221.COC1=C(O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)C=C(C=C1)[C@H]1OC2=C(C[C@H]1O)C(O)=CC(O)=C2222. COC1=C(O)C2=C(NC=C2CCNC(C)=O)C=C1O 223.CN(C)\C=N\c1nc(nc2sc(C#N)c(C)c12)-c1ccccc1 224.COC1=CC(O)=CC2=C1C(=O)C1=C(C=C(CO)C=C1O)C2=O 225.COC1=CC(CC2C(CC3=CC(OC)=C(O)C=C3)COC2=O)=CC=C1O 226.Cc1ccc(cc1)S(=O)(=O)\N=C(\Nc1ccc2[nH]c(=O)[nH]c2c1)c1ccccc1 227.COC1=CC(CC2COC(C2CO)C2=CC(OC)=C(O)C=C2)=CC=C1O 228.COC1=CC2=C(C(O)=C1OC)C(=O)C1=C(C(O)=C(C)C(O)=C1)C2=O 229.COC1=C2CC(COC2=C(C=O)C(O)=C1)C1=C2OC(C)(C)C=CC2=C(O)C=C1 230.CC1=CC2=C(C(O)=C1)C(=O)C1=C(C=C(O)C=C1O)C2=O 231.O[C@H]1[C@@H](O)C2=C(O[C@@H]1C1=CC=C(O)C=C1)C=C(O)C=C2O 232.COC1=CC(=CC=C1O)C(O)C(CO)OC1=C(OC)C=C(CC2C(CC3=CC(OC)=C(O)C=C3)COC2=O)C=C1233. OC1C(COC2=C1C=CC(O)=C2)C1=CC=C(O)C=C1O 234.COC1=CC2=C(C(O)=C1)C(=O)C1=C(O)C=C(C)C=C1C2=O 235.CC1(C)CCC2=C(O)C3=C(OC4=CC(O)=C5OC(C)(C)CCC5=C4C3=O)C=C2O1 236.COC1=C(OC)C(O)=C(C=C1)C(=O)\C=C\C1=CC=C(O)C=C1 237.Cc1sc2ncnc(NCCc3nc(C)cc(=O)[nH]3)c2c1C 238.COC1=CC2=C(C3C=COC3O2)C2=C1C(=O)C1=C(O2)C(OC)=C(OC)C=C1O 239.COC1=C2C(=O)CC(OC2=C(C)C(O)=C1C)C1=CC=CC=C1 240.Nc1c(C#N)c(=O)[nH]c2sc3CCCCc3c12 241.CCOc1ccc(cc1C)S(=O)(=O)Nc1ccc2NC(=O)C(C)(C)COc2c1 242.OC1C(O)C2=C(OC1C1=CC=C(O)C(O)=C1)C=C(O)C=C2O 243.CCCOc1ccc(cc1C)S(=O)(=O)Nc1ccc2N(C)C(=O)C(C)(C)COc2c1 244.COc1ccc(CCc2ccc(c(c2)OC)O)cc1O 245. COc1ccc(cc1O)[C@H]1Cc2cccc(c2CO1)O246. COC1=C(O)C2=C(C=C1O)C(=O)C1=C(C(O)=C(C)C=C1)C2=O 247.COC1=C(O)C=C2OC3=CC(O)=CC(O)=C3C(=O)C2=C1 248.COC1=C(CC=C(C)C)C(O)=C(C=C1)C1COC2=C(C=O)C(O)=CC(OC)=C2C1 249.CC1=CC(=O)C2=C(O)C3=C(O)C=C(O)C=C3C=C2O1 250.COC1=CC(\C=C/CO)=CC2=C1OC(C2CO)C1=CC(OC)=C(O)C=C1 251.OC1=CC(O)=C(C=C1)C1CC(=O)C2=C(O)C=C(O)C=C2O1 252.COC1=CC(=CC=C1O)C1OC2=CC=C3NC=C4CCNC(=O)C1C2=C34 253.COC1=C(O)C=CC(\C=C(/C)C(=O)C2=C(O)C=C(O)C=C2O)=C1 254.COC1=CC(=CC=C1O)C1OCC2C1COC21=CC(OC)=C(O)C=C1 255.COC1=C(O)C=CC(=C1)C1OCC2C1COC2C1=CC=C2OCOC2=C1 256.COC1=CC2=C(C(O)=C1CC=C(C)C)C(=O)C1=C(CC=C(C)C)C(OC)=C(O)C=C1O2 257.COC1=CC2=C(C=C1O)C(C(CO)C(CO)C2)C1=CC=C(O)C(OC)=C1 258.COC1=C2OC3=C(C=CC=C3O)C2=C(OC)C(O)=C1OC 259. NC(=N)c1ccc(NS(N)(=O)=O)cc1260. COC1=CC(=CC=C1O)C1OCC2C1COC21=CC=C2OCOC2=C1 261.Cc1c(sc2nc[nH]c(=O)c12)C(=O)Nc1ccccc1 262.COC1=CC(O)=C2C(=O)CC(OC2=C1)C1=C(OC)C=C(OC)C=C1OC 263.COc1ccc(cc1C)S(=O)(=O)Nc1ccc2N(CC=C)C(=O)C(C)(C)COc2c1 264.Nc1nc(=O)n(CC(=O)Nc2ccccc2)c2sc3CCCc3c12 265.CCOc1ccc(cc1OCC)S(=O)(=O)Nc1cccc(c1)C(\N)=N\O 266.Cc1ccc(cc1)C(\N)=N\S(=O)(=O)c1ccc(C)cc1 267.N\C(=N\O)c1ccc(Cl)cc1NS(N)(=O)=O 268.COC1=C(O)C2=C(C=C1O)C(=O)C1=C(C(O)=CC=C1)C2=O 269.N\C(=N\O)c1cc(Br)ccc1NS(N)(=O)=O 270.CC1(C)Cc2c(CS1)sc1[nH]c(=S)nc(N)c21 271.COc1ccc(NC(=O)Cn2c3sc4CCCc4c3c(N)nc2=O)cc1 272.CC(C)=CCC1=C(O)C=CC(C2COC3=C(C2)C=CC2=C3C=CC(C)(C)O2)=C1O 273.COc1ccc(NC(=O)Cn2c3sc4CCCCCc4c3c(N)nc2=O)cc1 274.COC1=C(OC)C2=C(C=C1)C(=O)C1=C(O)C(C3C(OC4=C3C3=C(C(O)=C4)C(=O)C4=C(N3C)C(O)=CC=C4)C(C)(C)O)=C(OC)C=C1N2275. CC1CCc2c(C1)sc1[nH]c(=S)nc(NCc3ccccc3)c21 276.COC1=C(CC=C(C)C)C(OC)=C(CC(=O)C2=C(O)C=C(O)C=C2)C(O)=C1 277.COC1=C(OC)C(CC=C(C)C)=C2C(=O)C3=C(OC2=C1)C=C(O)C(CC(O)C(C)=C)=C3O 278.OC1=CC2=C(C=C1)C1(O)COC3=C(C=CC(O)=C3)C1O2 279.CS(=O)(=O)Nc1ccc(cc1)C(\N)=N\OC(=O)Nc1ccccc1 280.N\C(=N\O)c1cc(Cl)cc(Cl)c1N 281.COC1=CC(O)=C2C(=O)C3=C(OC2=C1)C1=C(OC(C)(C)CC3)C=C(O)C=C1 282.Cc1oc2nc[nH]c(=O)c2c1C 283.COC1=CC(CC2COC(=O)C2CC2=CC(OC)=C(O)C=C2)=CC(C(CO)C(=O)C2=CC(OC)=C(O)C=C2)=C1O284. COC1=C2C(O)=C3C(=O)CC(C)(O)OC3=CC2=CC(O)=C1 285.CCc1c(C)sc2n(CC(=O)Nc3ccccc3OC)c(=O)nc(N)c12 286.Cc1sc2ncnc(NCCCc3nc(=O)[nH][nH]3)c2c1C 287.COc1ccccc1NC(=O)Cn1c2sc3CCCc3c2c(N)nc1=O 288.COC1=C(OC)C(CC=C(C)C)=CC(=C1)C1CC(=O)C2=C(O)C=C(O)C=C2O1 289.COC1=CC2=C(C(O)=C1C1C(OC3=C1C1=C(C(O)=C3)C(=O)C3=C(N1C)C(OC)=C(O)C=C3)C(C)(C)O)C(=O)C1=C(N2)C(OC)=C(OC)C=C1290. CCCOc1ccc(cc1C)S(=O)(=O)Nc1ccc2OCC(C)(C)C(=O)Nc2c1 291.NC(=N)c1cc(NS(N)(=O)=O)ccc1F 292.OCC1OC2=C(OC1C1=CC3=C(OC(C(CO)O3)C3=CC(O)=C(O)C=C3)C=C1)C=C(\C=C\C=O)C=C2293. COC1=C(C=CC(O)=C1CC=C(C)C)C1COC2=C(C1)C=CC(O)=C2 294.COC1=CC2=C(C(O)=C1)C(=O)C1=C(N2C)C2=C(OC(C)(CO2)\C=C\C2=C(O)C=CC3=C2OC(=O)C=C3)C=C1295. COC1=CC(\C=C\C(=O)NCCC2=CC(O)=C(OC)C=C2)=CC=C1O 296.OC1CC2=C(O)C=C(O)C=C2OC1C1=CC(O)=C(O)C=C1 297.CC(=C)C1CC2=CC3=C(OCC4(O)C3OC3=C4C=CC(O)=C3)C=C2O1 298.CN\C(=N/S(=O)(=O)c1cccc(c1)[N+]([O−])=O)c1ccccc1 299.Cc1nc(Nc2cccc(O)c2)c2c3CCCc3sc2n1

In specific embodiments, the present invention provides sweet tastemodulator compounds as shown in Table 3, as well as derivatives of thecompounds exemplified in Table 3. In preferred embodiments, thesecompounds are isolated or purified. Without being bound to anyparticular theory, these compounds and derivatives thereof have lowtoxicity to humans and are thus believed to be safe for uses on humans.

TABLE 3 SMILES structures[C@H]1(c2cc(c(c(c2)O)OC)O)[C@@H](Cc2c(O1)cc(cc2O)O)OCOc1cc(ccc1O)[C@H]1[C@@H](Cc2c(cc(cc2O1)O)O)OCOc1c(ccc(c1OC)O)[C@@H]1Cc2ccc(cc2OC1)OCOc1cc(ccc1O)[C@@H]1[C@@H](Oc2ccc(cc2O1)[C@H]1[C@H](C(═O)c2c(cc(cc2O1)O)O)O)COCOC1═C(O)C═C(C═C1)[C@@H]1CC(═O)C2═C(O)C═C(O)C═C2O1Cc1cc2c(c(c1)O)C(═O)c1c(cc(cc1O)O)C2═O Cc1cc2c(c(c1)O)C(═O)c1c(cccc1O)C2COC1═CC═C(C═C1)C1CC(═O)C2═C(O1)C═C(O)C═C2OOC1═CC═C(C═C1)C1CC(═O)C2═C(O1)C═C(O)C═C2OCOC1═CC(═CC═C1O)C1OC2═CC═C(C═C2OC1CO)C1OC2═CC(O)═CC(O)═C2C(═O)C1OCOC1═CC═C(C2COC3═CC(O)═CC═C3C2)C(O)═C1COC1═C(O)C═C(CC2COC3═CC(O)═CC(O)═C3C2═O)C═C1c1(cc(c(c(c1)O)OC)O)/C═C\c1cc(cc(c1)O)OCOC1═CC(O)═C2C(═O)CC(OC2═C1)C1═CC(O)═CC(O)═C1COC1═C(O)C═C2C(CC22COC3═CC(O)═CC(O)═C3C2═O)═C1c12c(OC[C@@H](C1═O)Cc1cc(c(cc1)O)O)cc(cc2OC)OCOC1═C(O)C(OC)═C(C═C1)C1COC2═CC(O)═CC═C2C1c12c(c(c(cc2O)OC)O)OC[C@@H](C1═O)Cc1ccc(cc1)Oc12c(O[C@H]([C@@H]1CO)c1cc(c(cc1)O)OC)c(ccc2[C@@H]1Oc2c(C(═O)C1)c(cc(c2)O)O)O1(c2cc(c(cc2)OC)O)[C@H](Cc2c(O1)cc(cc2O)OC)OCOC1═C(O)C═C(\C═C/C2═CC(O)═CC(O)═C2)C═C1OCOC1═C(O)C═C(CC2(O)OC3═C(C═CC(O)═C3)C2═O)C═C1 COC1═C(O)C(O)═C(C)C═C1OCOC(═O)C1═C(O)C═C(O)C═C1OCOc1cc(ccc1O)[C@H]1[C@H](c2c(ccc(c2O1)O)[C@H]1[C@@H](C(═O)c2c(cc(cc2O1)O)O)O)COCOc1ccc(c(c1OC)O)[C@H]1Cc2ccc(cc2OC1)O

Among the compounds disclosed herein, provided are several clusters ofcompounds with similar pharmacophores. Such clusters of compounds andderivatives thereof, can be used for enhancing sweet taste. Alsoprovided are ingestible compositions containing these compounds, andmethods of preparing such ingestible compositions.

In some embodiments, a compound has a core of

C(C(C(C(:C(:C(:C(C(OC[*:9])[*:8])[*:7])[*:6])[*:5])[*:4])[*:3])[*:2])[*:1],wherein R1-R8 are selected from the substituents listed in Table 1-A.

In some embodiments, a compound has a core of

c1c(O[*:3])c([*:4])c([*:6])c(C(C[*:1])[*:2])c1[*:5], wherein R1-R6 areselected from the substituents listed in Table 1-B. To give an example,a compound has a SMILES structure ofc12c(OC[C@@H](C1=O)Cc1cc(c(cc1)O)O)cc(cc2OC)O.

In some embodiments, a compound has a core of

C(:C(:C(:C(O[*:5])[*:4])[*:3])[*:2])[*:1], wherein R1-R5 are selectedfrom the substituents listed in Table 1-C. Exemplary compounds include,but are not limited to, the following:

SMILES structures [C@H]1(c2cc(c(c(c2)O)OC)O)[C@@H](Cc2c(O1)cc(cc2O)O)OCOc1cc(ccc1O)[C@H]1[C@@H](Cc2c(cc(cc2O1)O)O)OCOc1c(ccc(c1OC)O)[C@@H]1Cc2ccc(cc2OC1)Oc1(cc(c(c(c1)O)OC)O)/C═C\c1cc(cc(c1)O)O[C@@H]1(c2cc(c(cc2)OC)O)[C@H](Cc2c(O1)cc(cc2O)OC)OCOc1ccc(c(c1OC)O)[C@H]1Cc2ccc(cc2OC1)O

In some embodiments, a compound has a core ofC(:C1:C([*:4]):C([*:3]):C([*:2]):C([*:6]):C:1[*:5])[*:1], wherein R1-R6are selected from the substituents listed in Table 1-D. Exemplarycompounds include, but are not limited to, the following:

SMILES structuresCOc1cc(ccc1O)[C@@H]1[C@@H](Oc2ccc(cc2O1)[C@H]1[C@H](C(═O)c2c(cc(cc2O1)O)O)O)COc12c(O[C@H]([C@@H]1CO)c1cc(c(cc1)O)OC)c(ccc2[C@@H]1Oc2c(C(═O)C1)c(cc(c2)O)O)OCOc1cc(ccc1O)[C@H]1[C@H](c2c(ccc(c2O1)O)[C@H]1[C@@H](C(═O)c2c(cc(cc2O1)O)O)O)CO

In some embodiments, a compound has a core of

C(:C:C(:C(C[*:5]):C(:C[*:1])[*:2])[*:4])[*:3], wherein R1-R5 areselected from the substituents listed in Table 1-E. Exemplary compoundsinclude, but are not limited to, the following:

SMILES structures Cc1cc2c(c(c1)O)C(═O)c1c(cc(cc1O)O)C2═OCc1cc2c(c(c1)O)C(═O)c1c(cccc1O)C2

In some embodiments, a compound has a core of,C(:C(:C[*:2]):C(:C(C[*:5])[*:4])[*:3])[*:1], wherein R1-R5 are selectedfrom the substituents listed in Table 2-A.

In some embodiments, a compound has a core of

c1c([*:2])c([*:1])c([*:5])c([*:4])c1[*:3], wherein R1-R5 are selectedfrom the substituents listed in Table 2-B. Exemplary compounds include,but are not limited to, the following:

SMILES structures COC1═C(O)C═C(C═C1)[C@@H]1CC(═O)C2═C(O)C═C(O)C═C2O1COC1═CC═C(C═C1)C1CC(═O)C2═C(O1)C═C(O)C═C2OOC1═CC═C(C═C1)C1CC(═O)C2═C(O1)C═C(O)C═C2OCOC1═CC═C(C2COC3═CC(O)═CC═C3C2)C(O)═C1COC1═C(O)C═C(CC2COC3═CC(O)═CC(O)═C3C2═O)C═C1COC1═CC(O)═C2C(═O)CC(OC2═C1)C1═CC(O)═CC(O)═C1COC1═C(O)C═C2C(CC22COC3═CC(O)═CC(O)═C3C2═O)═C1COC1═C(O)C(OC)═C(C═C1)C1COC2═CC(O)═CC═C2C1c12c(c(c(cc2O)OC)O)OC[C@@H](C1═O)Cc1ccc(cc1)OCOC1═C(O)C═C(CC2(O)OC3═C(C═CC(O)═C3)C2═O)C═C1

In some embodiments, a compound has a core of

C(:C(:C(:C(:C[*:3])[*:4])[*:5])[*:2])[*:1], wherein R1-R5 are selectedfrom the substituents listed in Table 2-C. Exemplary compounds include,but are not limited to, the following:

SMILES structures COC1═C(O)C(O)═C(C)C═C1O COC(═O)C1═C(O)C═C(O)C═C1O

In some embodiments, a compound has a core of

C(c1c(O[*:1])c([*:2])c([*:3])c([*:4])c1[*:5])[*:6], wherein R1-R6 areselected from the substituents listed in Table 2-D.

In some embodiments, a compound has a core of

C(c1c([*:3])c([*:2])c([*:6])c([*:5])c1[*:4])[*:1], wherein R1-R6 areselected from the substituents listed in Table 2-E. Exemplary compoundsinclude, but are not limited to, the following:

SMILES structuresCOC1═CC(═CC═C1O)C1OC2═CC═C(C═C2OC1CO)C1OC2═CC(O)═CC(O)═C2C(═O)C1OCOC1═C(O)C═C(\C═C/C2═CC(O)═CC(O)═C2)C═C1O

Tab1e 1-A R1 R2 R3 R4 R5 R6 R7 R8 1. [H]Oc(:[*:1]): [H]O[*:2] [H][*:3][H][*:4] [H]Oc(:[*: [H][*:6]. [H]Oc(c(OC([H]) [H][*:8]. [*:5].[H][*:1]1]):[*:5] [H][*:6] ([H])[H])c [H][*:8] (O[H])c(C([H]) ([H])[H]):[*:9])c(C(═O) [*:7]):[*: 9].[H][*:7] 2. [H]C([H])(O [H]C([H]) [H][*:3][H][*:4] [H]Oc(:[*: [H][*:6]. [H]Oc(c([H])c(O[H]) [H][*:8] [*:1])O[*:2].(O[*:1])O 1]):[*:5] [H][*:6] c(c(═O):[*:7]):[*:9])c [H]Oc(:[*:1]): [*:2](C([H])([H])[H]): [*:5] [*:9] 3. [H]O[*:1].[H] [H]C([H]) [H][*:3][H][*:4] [H]c(:[*: [H][*:6]. [H]Oc(c([H])c(O[H])c [H][*:8].c(:[*:1]):[*:5] ([H])O[*:2] 1]):[*:5] [H][*:6] (C(═O)[*:7]):[*:9])c[H][*:8] (OC([H])([H])[H]): [*:9].[H][*:7] 4. O([*:1])[*:5]. [H]Oc(c(c[H][*:3]. [H][*:4]. O([*:1]) [H]Oc(c [H][*:7] [H]Oc(c [H]Oc(c(c([H]):([H]):[*:2]) [H][*:3] [H][*:4] [*:5]. ([H])c(O ([H])c(O[*: [*:2])C([H])C([H])([H]) [H][*:5] [*:9]):[*: 9]):[*:8]): ([H])[H])c(C [H])c(C8]):[*:6] [*:6] ([H])([H])[H]): ([H])([H]) [*:1] [H]):[*:1] 5.[H][*:1].[H]c [H]O[*:2] [H][*:3] [H][*:4] [H]c(:[*: [H][*:6].[H]Oc(c(c(O[H])c(C [H][*:8]. (:[*:1]):[*:5] 1]):[*:5] [H][*:6](═O)[*:7]):[*:9])C [H][*:8] ([H])([H])[H])c(OC ([H])([H])[H]):[*:9].[H][*:7] 6. [H]C([H]) [H]O[*:2] [H][*:3] [H][*:4] [H]c(:[*: [H][*:6].[H]Oc(c(OC([H]) [H][*:8]. ([H])O[*:1].[H]c 1]):[*:5] [H][*:6]([H])[H])c(O[H])c(C [H][*:8] (:[*:1]):[*:5] (═O)[*:7]):[*:9])c([H]):[*:9].[H][*:7] 7. [H]Oc(c([H])c [H][*:2]. [H][*:3]. O═[*:4][H]c(c(O [H]O[*:6] O([*:7])[*:9] [H]c(c(O ([H])c([H]): [H]c(c(O [H][*:3][*:2]):[*: [*:2]):[*: [*:1])c(O[H]): [*:2]):[*:5]): 5]):[*:8] 5]):[*:8][*:1] [*:8] 8. [H]Oc(c([H]) [H]Oc(c [H][*:3]. [H]C([H]) O═[*:5][H]Oc(c(c [H]C([H])(O[*:7])[*:4] [H]Oc(c(c c([H]):[*:2])c ([H])c([H]):[H][*:3] (O[*:7])[*: (OC([H]) (OC([H]) (O[H]):[*:1]. [*:2])c(O4].[H][*:4] ([H])[H]): ([H])[H]): [H][*:1] [H]):[*:1] [*:8]) [*:8])CC([H]) ([H])([H]) ([H])[H]): [H]):[*:6] [*:6] 9. [H]O[*:1].[H] [H]O[*:2][H][*:3] [H][*:4] [H]c(:[*: [H][*:6] [H]Oc(c([H])c(OC [H][*:8].c(:[*:1]):[*:5] 1]):[*:5] ([H])([H])[H])c(O[H]): [H][*:8][*:9])c(C(═O)[*:7]): [*:9].[H][*:7] 10. [H]C([H]) [H]C([H]) [H][*:3][H]O[*:4] O═[*:5] O═[*:6] [H]O[*:7].[H][*:7] [H]Oc1c ([H])O[*:1]([H])O[*:2] ([H])c([H]) c([*:8])c ([H])c1O [H].[H] [*:8] 11.[H]Oc(c([H]) [H]Oc(c [H][*:3]. [H]C([H]) O═[*:5] [H]Oc(c(c(O[H]C([H])(O[*:7]) [H]Oc(c(c c(OC([H])([H]) ([H])c(OC [H][*:3](O[*:7])[*: [H]):[*:8])C [*:4] (O[H]):[*: [H])c([H]): ([H])([H])4].[H][*:4] ([H])([H]) 8])C([H]) [*:1]):[*:2]. [H])c([H]):[*: [H]):[*:6]([H])[H]): [H][*:1] 1]):[*:2] [*:6] 12. [H]O[*:1].[H] [H]Oc(cO([*:3])[*: [H][*:4]. O([*:1]) [H]Oc(c O([*:3])[*:7] [H]Oc(c Oc(c([H])c([H])c([H]): 7].[H][*:3] [H][*:4] [*:5] ([H])c(O ([H])c(OC ([H]):[*:1])c[*:1])c([H]): C([H]) ([H])([H]) ([H]):[*:2] [*:2] ([H])[H]):[H]):[*:8]): [*:8]):[*:6] [*:6] 13. O([*:1])[*:5]. [H][*:2]. O═[*:3][H]Oc(:[*: [H]C([H]) [H][*:6] [H]O[*:7] [H]Oc(:[*: [H]Oc1c([H]) [H][*:2]4]):[*:8] ([N+]([H]) 4]):[*:8] c([H])c(O[H]) (C([H])([H]) c([*:1])c1[H].[*:3])C [H][*:1] ([H])([H]) [*:5])[*:1] 14. [H]C([H])([N+] [H]Oc(c(OC[H]C([H])([N+] [H]c(:[*: O═[*:5] [H][*:6] [H]O[*:7] [H]c(:[*:([H])(C([H]) ([H])([H]) ([H])(C([H]) 4]):[*:8] 4]):[*:8] ([H])[*:3])C[H])c(OC ([H])[*:3])C ([H])([H])[*:5]) ([H])([H]) ([H])([H])[*:5])[*:1].[H]Oc(c [H])c([H]): [*:1].[H][*:3] (OC([H])([H]) [*:2]):[*:1][H])c(OC([H]) ([H])[H])c ([H]):[*:2]): [*:1] 15. [H]Oc(c([H]) [H]Oc(cO([*:3])[*:7]. [H]O[*:4]. O([*:1]) [H]Oc(c1c O([*:3])[*:7] [H]Oc(c1c(OC([H])([H]) ([H])c(OC [H][*:3] [H][*:4] [*:5] (:[*:8]) c(:[*:8])O[H]):[*:1])c ([H])([H]) OC([H]) C([H])([H])O1): ([H]):[*:2].[H][H]):[*:1])c ([H])O1): [*:6] [*:1] ([H]):[*:2] [*:6] 16. O([*:1])[*:5].[H][*:2]. O═[*:3] [H]Oc(:[*: [H]c(c(C [H][*:6] [H]O[*:7] [H]Oc(:[*:[H]Oc1c([H]) [H][*:2] 4]):[*:8] ([H])([H]) 4]):[*:8] c([H])c([*:1])C([H])([H]) c([H])c1O[H]. N(C(═O) [H][*:1] [*:1])[*: 4]):[*:5]): [*:8]17. [H]Oc(c(OC [H]Oc(c(O [H][*:3]. [H][*:4]. [H][*:5] [H][*:6] [H]O[*:7][H]c(c(C ([H])([H])[H])c C([H])([H]) [H][*:3] [H]c(c(C([H]) ([H])([H])(O[H]):[*:1])c [H])o(O[H]): ([H])C([H]) C([H])([H])N ([H]):[*:2].[*:1])c([H]): ([H])N(C (C(═O) [H]c(c(C([H]) [*:2] (═O)[*:1])[*:[*:1])[*: ([H])C([H]) 4]):[*:5]): 4]):[*:5]): ([H])N(C(═O)[*: [*:8][*:8] 1])[*:4]):[*:5]):[*:8] 18. [H]Oc1c(C [H]Oc1c(C [H][*:3].[H]c(:[*:4]): [H]O[*:5] [H][*:6] O([*:7])[*:9] [H]c(:[*: ([H])═O)c(O([H])═O)c(O [H][*:3] [*:8] 4]):[*:8] [H])c(c(═O):[*: [H])c(c(═O):2])c(o:[*:1])c1 [*:2])c(o: C([H])([H]) [*:1])c1 [H].[H][*:1]C([H])([H])[H] 19. [H]Oc1c(C [H][*:2]. [H][*:3]. [H]c(:[*:4]): O([*:1])[H][*:6] O([*:7])[*:9] [H]c(:[*: ([H])([H])[H])c [H][*:2] [H][*:3] [*:8][*:5] 4]):[*:8] ([H])c([*:1])c (O[H])c1C ([H])([H])[H].[H][*:1].[H][*:1] 20. O([*:1])[*:5]. [H][*:2]. O═[*:3] [H]Oc(:[*:[H]c(:[*: [H][*:6] [H]C([H])([H])O[*: [H]Oc(:[*: [H]Oc1c([H]) [H][*:2]4]):[*:8] 1]):[*:5] 7] 4]):[*:8] c([H])c(O[H]) c([*:1])c1[H]. [H][*:1]21. [H][*:1].[H]c [H]C([H]) [H][*:3] [H][*:4] O═[*:5] [H][*:6].[H]Oc(c(c(O[H])c(C [H][*:8]. (:[*:1]):[*:5] ([H])O[*:2] [H][*:6](═O)[*:7]):[*:9])C [H][*:8] ([H])([H])[H])c (OC([H])([H])[H]):[*:9].[H][*:7] 22. [H]Oc(c([H]) [H]Oc(c O([*:3])[*:7]. [H][*:4].O([*:1]) [H]Oc(c O([*:3])[*:7] [H]Oc(c c([H]):[*:2])c ([H])c([H]):[H][*:3] [H][*:4] [*:5] (OC([H]) (OC([H]) ([H]):[*:1]. [*:2])c([H])([H])[H]) ([H])[H])c [H][*:1] c(OC([H]) (OC([H]) ([H])[H]): ([H])[H]):[*:8]): [*:8]):[*:6] [*:6] 23. O([*:1])[*:5]. [H]Oc1c O═[*:3] [H]Oc(:[*:[H]O[*:5] [H]C [H]C([H]) [H]Oc(:[*: [H][*:1].[H] ([H])c([H])c 4]):[*:8]([H]) ([H])O[*:7] 4]):[*:8] [*:1] (C([H])([H]) ([H])O [*:2])c([H])c1[*:6] [H].[H][*:2] 24. [H]Oc1c([H]) [H][*:2]. [H]Oc1c([H])c[H]c(:[*:4]): O([*:1]) [H][*:6] O([*:7])[*:9] [H]c(:[*: c(C([H])([H])[H][*:2] (C([H])([H])[H])c [*:8] [*:5] 4]):[*:8] [H])c([*:1])c([*:1])c(O[*: (O[*:3])c1C 3])c1C([H]) ([H])([H])[H]. ([H])[H].[H][*:3][H][*:1].[H][*:1] 25. O([*:1])[*:5]. [H][*:2]. O═[*:3] [H]Oc(:[*:[H][*:6] [H]C([H]) [H]Oc(:[*: [H]Oc1c([H]) [H][*:2] 4]):[*:8]([H])O[*:7] 4]):[*:8] c([*:1])c([H]) c([H])c1OC ([H])([H])[H]. [H][*:1]26. [H]C([H]) [H]O[*:2] [H]C([H])([H]) [H]O[*:4] [H]C([H]) O═[*:6][H][*:7]. [H]Oc1c ([H])[*:1] [*:3] ([N+]([H]) [H][*:7] ([H])c([H])c(C([H])([H]) ([*:8])c [*:3])C([H]) ([H])c1O ([H])[*:5]) [H].[H][*:8][*:1] 27. [H]C([H]) [H]Oc(c(O [H]C([H])([N+] [H]c(:[*:4]): [H][*:6][H]O[*:7] [H]c(:[*: ([N+]([H1)(C([H]) O([H1)([H]) ([H])(C([H])([H])[*:8] 4]):[*:8] ([H])[*:3])C [H])c(OC [*:3])C([H]) ([H])([H])[*:5])([H])([H]) ([H])[*:5])[*: [*:1].[H]Oc(c [H])c([H]): 1].[H][*:3](OC([H])([H]) [*:2]):[*:1] [H])c(OC([H]) ([H])[H])c ([H]):[*:2]): [*:1]28. [H]C([H]) [H]O[*:2] [H]C([H])([H]) [H]O[*:4] [H]C([H]) O═[*:6][H][*:7].[H][*:7] [H]Oc1c ([H])[*:1] [*:3] ([*:3])[*: ([H])c([H]) 5]c([*:8])c ([H])c1O [H].[H][*:8] 29. [H]Oc(c([H]) O═[*:2][H]C([H])([*:3]) [H]c(:[*:4]): [H]Oc(c([H]) [H][*:6] [H]O[*:7] [H]c(:[*:c(O[H]):[*:1]) [*:5].[H]Oc(c [*:8] c(OC([H]) 4]):[*:8] c([H])c(OC([H])([H])c(O[H]): ([H])[*:5]): ([H])[*:3]) [*:1])c([H])c(O [*:3]):[*:1].:[*:1] C([H])([H])[*: [H][*:5] 3]):[*:1] 30. [H]Oc(c([H]) [H]O[*:2][H]Oc(c([H])c O═[*:4] [H]c(:[*:1]): [H]Oc [H]C([H])([H])O [H]Oc(cc(OC([H])([H]) (OC([H])([H]) [*:5] (c([H])c [*:7] ([H])c([H])[*:5]):[*:3]): [*:5]):[*:3]): ([H]):[*:6]): 8] [*:1].[H][*:1] [*:1][*:8] 31. [H]C([H])([H]) [H]O[*:2] [H][*:3] [H]O[*:4] [H][*:5] [H][*:6].[H]Oc(c([H])c(O[H]) [H][*:8]. O[*:1].[H]c(: [H][*:6]c(C(═O)[*:7]):[*:9]) [H][*:8] [*:1]):[*:5] c([H]):[*:9] 32. [H][*:1][H][*:2] [H]C([H])([H]) [H]O[*:4] [H][*:5] [H]Oc(c([H])c(O[H]) [H][*:8].O[*:3] c(C(═O)[*:7]):[*:9]) [H][*:8] c([H]):[*:9].[H][*:7] 33. [H][*:2][H]C([H])([H]) [H]O[*:4] [H]C([H]) [H]Oc(c([H])c(O[H]) [H][*:8]. O[*:3]([H])O[*: c(C(═O)[*:7]):[*:9]) [H][*:8] 5] c([H]):[*:9].[H][*:7] 34.[H][*:1] [H][*:2] [H]C([H])([H]) [H]Oc(:[*: [H]C([H]) [H][*:6][H]Oc(c([H])c(O[H]) [H][*:8]. O[*:3] 4]):[*:8] ([*:3])[*:c(C(═O)[*:7]):[*:9]) [H][*:8] 5] c([H]):[*:9].[H][*:7] 35. [H]Oc(c([H])O═[*:2] [H]C([H])([*:3]) [H]c(:[*:4]): [H]C([H]) [H][*:6] [H][*:7][H]Oc(: c(OC([H])([H]) [*:5].[H]Oc(c [*:8] ([*:3])[*: [*:4]):[*:8][H])c([H])c ([H])c(OC([H]) 5] (OC([H])([H]) ([H])[H])c([H])[*:3]):[*:1]): c(OC([H])([H]) [*:1] [*:3]):[*:1]): [*:1] 36.[H]Oc(c([H]) O═[*:2] [H]C([H])([*:3]) O═[*:4] [H][*:5]. [H]c(c[H]C([H])([H])O [H]c(:[*: c(O[H]):[*:1]) [*:5].[H]Oc(c [H][*:5] ([H]):[*:7] 4]):[*:8] c([H])c(OC([H]) ([H])c(O[H]): [*:6])c ([H])[*:3])[*:1])c([H])c(O (OC([H]) C([H])([H])[*: ([H])[H]): 3]):[*:1] [*:8] 37.[H]Oc(c([H]) [H]O[*:2] [H]Oc(c([H])c [H]c(:[*:4]): [H]C([H]) [H][*:6][H][*:7] [H]c(c([H]): c(O[H]):[*:3]) (O[H]):[*:3]): [*:8] ([*:3])[*:5][*:6])c(OC [*:1] ([H])([H]) [H]):[*:8] 38. [H]Oc(c([H]) O═[*:2][H]C([H])([*:3]) [H]c(:[*:4]): [H][*:5] [H][*:6] [H]O[*:7] [H]c(:[*:c(OC([H])([H]) [*:5].[H]Oc(c [*:8] 4]):[*:8] [H])c([H])c ([H])c(OC([H])(OC([H])([H]) ([H])[H])c([H]) [*:3]):[*:1]): c(OC([H])([H]) [*:1][*:3]):[*:1]): [*:1] 39. [H]Oc(c([H]) O═[*:2] [H][*:3]. [H]O[*:4]O═[*:6] [H]C([H])(O[*:7])C [H]c(:[*: c(O[H]):[*:1]) [H][*:3]([H])([H])[*:9] 4]):[*:8] c([H])c(O[H]): [*:1] 40. [H][*:1] [H]C([H])[H][*:3] [H][*:4] [H][*:5] [H][*:7].[H][*:7] [H]Oc1c ([H])O[*:2]([H])c([H]) c([H])c ([*:8])c1O [8] 41. [H]O[*:1] [H][*:2] [H]O[*:3][H]O[*:4] [H]Oc(: O═[*:6] [H]Oc(c(c(OC([H]) [H][*:8]. [*:1]):[*:5]([H])[H])c(C([H]) [H][*:8] ([H])[*:7]):[*:9])C ([H])([H])C([H])═C(C([H]) ([H])[H])C([H]) ([H])[H])c([H]): [*:9].[H][*:7] 42.[H]Oc(:[*:1]): [H]O[*:2] [H][*:3] [H]O[*:4] [H][*:5] [H]C[H][*:7].[H][*:7] [H]c(c([H]): [*:5].[H][*:1] ([H]) [*:9]):[*:8] ([H])O[*:6] 43. [H]Oc1c([H]) O═[*:2] [H]C([H])([H]) o(:[*:1]): [H]Oc(c[H][*:6] [H]C([H])([H])O [H]Oc(c c([H])c(C([H])= O[*:3] [*:4]([H]):[*:5]): [*:7] ([H]):[*:5]): [*:1])c([H]) [*:8] [*:8]c1O[H].[H][*:1] 44. [H]Oc(c([H]) [H]Oc(c([H]) [H]O[C@] [H][*:5][H]O[*:6] [H]O[*:7] c([H]):[*:1])c c([H]):[*:1]) ([H])(O[*:4])([H]):[*:2].o(: c([H]):[*:2] [*:1] [*:1]):[*:4] 45. [H]O[C@]([H])[H]C([H])([H]) [H]O[C@ [H][*:5] [H]O[*:6] [H]O[C@]([H])(C (O[*:4])[*:1].[*:2].[H][*:2] @]([H])(O ([H])([H])[*:7])[*:9] [H][*:1].[H] [*:4])[*:1][*:1] 46. [H]O[C@@] [H]C([H])([H]) [H]C([H])([H]) [H]C([H]) [H]C([H])[H][*:6] [H]O[C@]([H])(C [H]C([H]) ([H])(O[*:4]) [*:2].[H][*:2][N+]([H])(C([H]) ([H])Oc(:[*: ([H])[N+] ([H])([H])[*:7])[*:9] ([H])Oc(:[H][*:1] ([H])C([H]) 4]):[*:8] ([H])(C([H]) [*:4]):[*: ([H])[*:5])[*:([H])C 8] 3].[H][*:3] ([H])([H]) [*:5])[*:3] 47. [H]Oc(c([H])[H]Oc(c([H]) [H]C([H])([H]) [H]C([H]) [H]C([H]) [H][*:6] O([*:7])[*:9][H]C([H]) c(O[H]):[*:2]) c(O[H]): [N+]([H])(C([H]) ([H])Oc(:[*:([H])[N+] ([H])Oc(: c([H]):[*:1]. [*:2])c([ ([H])C([H]) 4]):[*:8]([H])(C([H]) [*:4]):[*: [H][*:1] ([H])[*:5])[*: ([H])C 8] 3].[H][*:3]([H])([H]) [*:5])[*:3] 48. [H]Oc(c([H]) [H]Oc(c([H]) [H][*:3].[H]c(:[*:4]): [H][*:5] [H][*:6] O([*:7])[*:9] [H]c(:[*: c(O[H]):[*:2])c(O[H]): [H][*:3] [*:8] 4]):[*:8] c([H]):[*:1]. [*:2])c [H][*:1]([H]):[*:1] 49. [H]Oc(c([H]) O═[*:2] O([*:7])[*:9] c(O[H]):[*:1])c(c([H]):[*:1]) C([H])([H])C ([H])([H])C([H]) ([H])[H]

TABLE 1-B R1 R2 R3 R4 R5 R6 1. O═[*:1]•[H]Oc1c([H])c(OC([H])[H]Oc1c([H])c(OC([H])([H]) [H][*:3] [H][*:4] [H][*:5] [H]C([H])([H])([H])[H])c([H])c(OC([H]) [H])c([H])c(OC([H])([H]) O[*:6]([H])[*:2])c1[*:1] [*:2])c1[*:1]•[H][*:2] 2. O([*:1])[*:5]•[H][*:1]•[H][H]Oc1c([H])c(O[H])c(C([H]) [H][*:3] [H][*:4] O([*:1])[*:5] [H][*:6][*:1] ([H])[*:2])c(OC([H])([H]) [H])c1[H]•[H][*:2] 3.[H]C([H])(O[*:5])[*:1]•[H] [H][*:2]•[H][*:2] [H][*:3] [H][*:4] [H]C([H])[H]C([H])([H]) Oc1c([H])c(OC([H])([H])[H]) (O[*:5])[*:1] O[*:6]c([H])c([H])c1[*:1]•[H][*:1] 4. [H][*:1]•[H][*:1]•[H]c1c(OC([H])[H][*:2]•[H]c1c(OC([H])([H]) [H][*:3] [H][*:4] [H]O[*:5] [H][*:6]([H])[H])c([H])c(O[*:1]) [H])c([H])c(O[*:1])c(C([H])c(C([H])([H])[*:2])c1OC([H1) ([H])[*:2])c1OC([H])([H]) ([H])[H] [H] 5.[H][*:1]•[H][*:1]•[H]c1c([H]) O═[*:2] [H][*:3] [H][*:4] [H]O[*:5][H]C([H])([H]) c(C([H])([H])[*:1])c([H]) O[*:6] c2c1OC([H])([H])O2 6.[H]Oc1c([H])c(OC([H])([H]) [H][*:2]•[H][*:2] [H][*:3] [H][*:4] [H][*:5][H][*:6] [*:1])c(C(═O)[*:1])c(O[H]) c1OC([H])([H])[H]•[H][*:1] 7.[H]C([H])(O[*:6])[*:1]•[H] O═[*:2] [H][*:3] [H][*:4] [H]C([H])[H]C([H])(O[*:6]) Oc1c([H])c([H])c(C([H])([H]) ([H])O[*:5] [*:1][*:1])c([H])c1O[H]•[H][*:1] 8. [H]C([H])(O[*:6])[*:1]•[H] O═[*:2][H][*:3] [H][*:4] [H]O[*:5] [H]C([H])(O[*:6])Oc1c([H])c(C([H])([H])[*:1]) [*:1] c([H])c([H])c1OC([H])([H])[H]•[H][*:1] 9. [H]Oc1c(OC([H])([H])[H]) [H][*:2]•[H][*:2] [H][*:3][H][*:4] [H][*:5] [H][*:6] c([H])c(O[H])c(C(═O)[*:1])c1OC([H])([H])[*:1]•[H][*:1] 10. [H]Oc1c([H])c(OC([H])([H])[H][*:2]•[H][*:2] [H][*:3] [H][*:4] [H][*:5] [H][*:6][*:1])c(C(═O)[*:1])c(O[H]) c1OC([H])([H])[H]•[H][*:1] 11.[H][*:1]•[H][*:1]•[H] [H][*:2]•[H][*:2] [H][*:3] [H][*:4] [H][*:5][H]O[*:6] c1c2c(c([H])c(C([H])([H])[*:1]) c1OC([H])([H])[H])OC([H])([H])O2 12. [H][*:1]•[H][*:1]•[H] [H][*:2]•[H][*:2] [H][*:3] [H]C([H])[H][*:5] [H]O[*:6] c1c2c(c([H])c(C([H])([H])[*:1]) ([H])[*:4]c1OC([H])([H])[H])OC([H]) ([H])O2 13. [H]C([H])(O[*:6])[*:1]•[H][H][*:2]•[H][*:2] [H][*:3] [H]C([H]) [H][*:5] [H]C([H])(O[*:6])Oc1c([H])c([H])c(C([H])([H]) ([H])O[*:4] [*:1][*:1])c([H])c1[H]•[H][*:1] 14. [H]Oc1c([H])c([H])c(C(═O)[H][*:2]•[H][*:2] [H][*:3] [H][*:4] [H]C([H]) [H]C([H])([H])[*:1])c([H])c1[H]•[H] ([H])O[*:5] O[*:6] [*:1]•[H][*:1] 15.[H]Oc1c([H])c([H])c(C([H]) [H][*:2]•[H][*:2] [H][*:3] [H]C([H]) [H][*:5][H]O[*:6] ([H])[C@@]([H])(C([H]) ([H])O[*:4]([H])OC(═O)[*:1])[*:1])c([H]) c1OC([H])([H])[H]•[H][*:1] 16.[H]Oc1c([H])c(OC([H])([H]) [H]Oc1c([H])c(OC([H])([H]) [H][*:3] [H][*:4][H][*:5] [H][*:6] [H])c(C([H])([H])[H]) [H])c(C([H])([H])[H])c(O[*:2])c(O[*:2])c1C([H])([H])[*:1]•[H] c1C([H])([H])[*:1]•[H][*:2][*:1]•[H][*:1] 17. [H]C([H])([H])[*:1]•[H] O═[*:2] [H][*:3] [H][*:4][H]Oc1c([H]) [H]O[*:6] Oc1c([H])c([H])c([C@@]([H]) c([H])c([C@@](O[*:5])[*:1])c([H])c1[H]•[H] ([H])(O[*:5])[*:1]) [*:1] c([H])c1[H] 18.[H]Oc1c([H])c([H])c(C(═O) [H][*:2]•[H][*:2] [H][*:3] [H]C([H]) [H][*:5][H][*:6] [*:1])c(O[H])c1[H]•[H] ([H])O[*:4] [*:1]•[H][*:1] 19.[H]C([H])(O[*:6])[*:1]•[H] [H][*:2]•[H][*:2] [H][*:3] [H]C([H]) [H][*:5][H]C([H])(O[*:6]) Oc1c([H])c([H])c(C([H])([H]) ([H])O[*:4] [*:1][*:1])c([H])c1[H]•[H][*:1] 20. [H]Oc1c([H])c(OC([H])([H])[H]Oc1c([H])c(OC([H])([H]) [H][*:3] [H][*:4] [H][*:5] [H][*:6][H])c(C([H])([H])[H])c(O[*:2]) [H])c(C([H])([H])[H])c(O[*:2])c1C([H])([H])[*:1]•[H] c1C([H])([H])[*:1]•[H][*:2] [*:1]•[H][*:1] 21.[H]Oc1c([H])c([H])c([C@@] [H][*:2]•[H][*:2] [H][*:3] [H][*:4][H]C([H])([H]) [H]Oc1c([H])c([H]) ([H])(O[*:6])[*:1])c([H]) O[*:5]c([C@@]([H]) c1[H]•[H][*:1]•[H][*:1] (O[*:6])[*:1])c([H]) c1[H] 22.[H]Oc1c([H])c([H])c([C@] [H][*:2]•[H][*:2] [H][*:3] [H]C([H])[H]C([H])([H]) [H]Oc1c([H])c([H]) ([H])(O[*:6])[*:1])c([H])c1[H]([H])[*:4] O[*:5] c([C@]([H])(O[*:6]) [H][*:1]•[H][*:1][*:1])c([H])c1[H] 23. [H]C([H])(O[*:5])[*:1]•[H] [H]O[*:2]•[H][*:2][H][*:3] [H][*:4] [H]C([H]) [H][*:6] O[*:1]•[H]Oc1c([H])c([H])(O[*:5])[*:1] c(C([H])([H])[*:1])c([H]) c1OC([H])([H])[H] 24.[H]C([H])(O[*:6])[*:1]•[H] [H]O[*:2]•[H][*:2] [H][*:3] [H][*:4] [H][*:5][H]C([H])(O[*:6]) O[*:1]•[H]Oc1c([H])c([H]) [*:1]c(C([H])([H])[*:1])c([H]) c1OC([H])([H])[H] 25. [H][*:1]•[H][*:1]•[H]O═[*:2] [H][*:3] [H][*:4] [H]O[*:5] [H]O[*:6]c1c([H])c(O[*:1])c([H])c([H]) c1OC([H])([H])[H] 26.[H]Oc1c([H])c(C([H])([H]) [H][*:2]•[H][*:2] [H][*:3] [H][*:4] [H][*:5][H][*:6] [*:1])c(OC([H])([H])[*:1]) c(rH])c1OC([H])([H])[H]•[H] [*:1]27. [H]Oc1c([H])c(OC([H])([H]) [H][*:2]•[H][*:2] [H][*:3] [H][*:4][H][*:5] [H][*:6] [H])c(C([H])([H])[H])c(OC([H])([H])[H])c1C(═O)[*:1]•[H] [*:1]•[H][*:1] 28. [H]C([H])(O[*:5])[*:1]•[H][H][*:2]•[H][*:2] [H][*:3] [H][*:4] [H]C([H]) [H]C([H])([H])Oc1c([H])c([H])c(C([H])([H]) (O[*:5])[*:1] O[*:6][*:1])c([H])c1[H]•[H][*:1] 29. [H]O[*:1]•[H]Oc1c([H])c([H])[H][*:2]•[H][*:2] [H][*:3] [H][*:4] [H]C([H])([H]) [H]Oc1c([H])c([H])c([C@@]([H])(O[*:6])[*:1]) O[*:5] c([C@@]([H])(O[*:6])c([H])c1[H]•[H][*:1] [*:1])c([H])c1[H] 30. [H]C([H])([H])[*:1]•[H]O═[*:2] [H][*:3] [H][*:4] [H]O[*:5] [H]Oc1c([H])c([H])Oc1c([H])c([H])c([C@@]([H]) c([C@@]([H])(O[*:6])(O[*:6])[*:1])c([H])c1[H]•[H] [*:1])c([H])c1[H] [*:1] 31.[H]Oc1c([H])c([H])c(C(═O) [H][*:2]•[H][*:2] [H][*:3] [H][*:4] [H]O[*:5][H]C([H])([H])O[*:6] [*:1])c([H])c1[H]•[H][*:1]•[H] [*:1] 32.[H]Oc1c([H])c([H])c(C([H]) O═[*:2] [H][*:3] [H]C([H]) [H][*:5] [H]O[*:6]([H])[*:1])c([H])c1[H]•[H] ([H])O[*:4] [*:1]•[H][*:1] 33.[H]Oc1c([H])c([C@]([H]) [H][*:2]•[H][*:2] [H][*:3] [H][*:4] [H][*:5][H]Oc1c([H])c([C@] (O[*:6])[*:1])c([H])c([H]) ([H])(O[*:6])[*:1])c1OC([H])([H])[H]•[H][*:1]•[H] c([H])c([H])c1OC([H]) [*:1] ([H])[H] 34.[H]C([H])(O[*:6])[*:1]•[H] [H]O[*:2]•[H][*:2] [H][*:3] [H][*:4] [H][*:5][H]C([H])(O[*:6]) Oc1c([H])c([H])c([*:1])c(OC([H]) [*:1]([H])[H])c1[H]•[H][*:1] 35. [H]Oc1c([H])c(C([H])([H]) [H][*:2]•[H][*:2][H][*:3] [H][*:4] [H][*:5] [H][*:6] [*:1])c(OC([H])([H])[*:1])c([H])c1OC([H])([H])[H]•[H] [*:1] 36. [H]C([H])([H])[*:1]•[H][H][*:2]•[H]c1c([H])c(O[*:1]) [H][*:3] [H][*:4] [H][*:5] [H]O[*:6][*:1]•[H]c1c([H])c(O[*:1]) c(O[*:2])c([H])c1C#CC([H])c(O[*:2])c([H])c1C#CC([H])([H]) ([H])[H] [H] 37.[H]Oc1c([H])c(OC([H])([H]) [H][*:2]•[H][*:2] [H][*:3] [H][*:4] [H][*:5][H][*:6] [H])c(OC([H])([H])[*:1]) c(C([H])([H])[*:1])c1[H]•[H] [*:1] 38.[H]C([H])([H])[*:1]•[H] [H][*:2]•[H]c1c([H])c(O[*:1]) [H][*:3] [H][*:4][H][*:5] [H]O[*:6] [*:1]•[H]c1c([H])c(O[*:1]) c(O[*:2])c([H])c1C#CC([H])c(O[*:2])c([H])c1C#CC([H])([H]) ([H])[H] [H] 39.[H]Oc1c([H])c(O[H])c(C(═O) [H][*:2]•[H][*:2] [H][*:3] [H][*:4] [H][*:5][H][*:6] [*:1])c(O[H])c1[H]•[H] [*:1]•[H][*:1] 40.[H]Oc1c([H])c([H])c([H]) [H][*:2]•[H][*:2] [H][*:3] [H]O[*:4] [H][*:5][H][*:6] c(OC([H])([H])[*:1])c1C(═O)[ [*:1]•[H][*:1] 41.[H]O[*:1]•[H]Oc1c([H])c([H]) [H][*:2]•[H][*:2] [H][*:3] [H]C([H])[H][*:5] [H][*:6] c(C([H])([H])[*:1])c(OC([H]) ([H])O[*:4]([H])[H])c1[H]•[H][*:1] 42. [H][*:1]•[H][*:1]•[H]c1c([H]) O═[*:2][H][*:3] [H][*:4] [H]O[*:5] [H]O[*:6] c([H])c([*:1])c(OC([H])([H])[H])c1[H] 43. [H]Oc1c([H])c([H])c([*:1]) [H]Oc1c([H])c([H])c([*:1])[H]C([H]) [H][*:4] [H]O[*:5] [H][*:6] c(OC([H])([H])[*:2])c1[H]•[H]c(OC([H])([H])[*:2])c1[H]•[H] ([H])[*:3] [*:1]•[H][*:1] [*:2] 44.[H]Oc1c([H])c(OC([H])([H]) [H][*:2]•[H][*:2] [H]C([H]) [H][*:4] [H][*:5][H][*:6] [H])c([H])c(O[H])c1C(═O) ([H])[*:3] [*:1]•[H][*:1]•[H][*:1] 45.[H]OC([H])([H])[*:1]•[H] [H]Oc1c([H])c([H])c(C([H]) [H][*:3] [H]O[*:4][H][*:5] [H][*:6] Oc1c([H])c([H])c(C([H])([H])([H])[C@]([H])(C([H])([H]) [C@]([H])(C([H])([H])O[*:2])O[*:2])[*:1])c([H])c1OC([H]) [*:1])c([H])c1OC([H])([H])([H])[H]•[H][*:2] [H]•[H][*:1] 46. [H]Oc1c([H])c(C([H])═[*:1]) O═[*:2][H]C([H]) [H][*:4] [H]C([H])([H]) [H]O[*:6] c([H])c([H])c1OC([H])([H])([H])[*:3] O[*:5] [H]•[H][*:1] 47. [H]Oc1c([H])c([H])c([*:1])[H]Oc1c([H])c([H])c([*:1]) [H]C([H]) [H][*:4] [H]O[*:5] [H][*:6]c(OC([H])([H])[*:2])c1[H]•[H] c(OC([H])([H])[*:2])c1[H]•[H] ([H])[*:3][*:1]•[H][*:1] [*:2] 48. [H]Oc1c([H])c([H])c(C([H])═[*:1]) O═[*:2][H]C([H]) [H][*:4] [H]C([H])([H]) [H]O[*:6] c([H])c1OC([H])([H])([H])[*:3] O[*:5] [H]•[H][*:1] 49. [H]Oc1c([H])c([H])c(C([H])[H]C([H])([H])[N+]([H]) [H]C([H]) [H]O[*:4] [H]C([H])([H]) [H][*:6]([H])[*:1])c([H])c1OC([H]) (C([H])([H])C([H])([H]) ([H])[*:3][N+]([H])(C([H]) ([H])[H]•[H][*:1]•[H][*:1] [*:5])[*:2]•[H][*:2]([H])C([H])([H]) [*:5])[*:2] 50. [H]Oc1c([H])c([H])c(C([H])[H]C([H])([H])[N+]([H]) [H]C([H]) [H]O[*:4] [H]C([H])([H]) [H][*:6]([H])[*:1])c([H])c1OC([H]) (C([H])([H])C([H])([H]) ([H])[*:3][N+]([H])(C([H]) ([H])[H]•[H][*:1]•[H][*:1] [*:5])[*:2]•[H][*:2]([H])C([H])([H]) [*:5])[*:2] 51. [H]OC([H])([H])[*:1]•[H][H]Oc1c([H])c([H])c(C([H]) [H][*:3] [H]O[*:4] [H][*:5] [H][*:6]Oc1c([H])c([H])c(C([H])([H]) ([H])[C@@]([H]) [C@@]([H])(C([H])([H])(C([H])([H]) O[*:2])[*:1])c([H])c1OC([H]) O[*:2])[*:1])c([H])c1OC([H])([H])[H]•[H][*:1] ([H])[H]•[H][*:2] 52. [H][*:1]•[H][*:1]•[H]c1c([H])O═[*:2] [H]C([H]) [H]C([H]) [H]O[*:5] [H]O[*:6]c([H])c(C([H])([H])[*:1]) ([H])[*:3] ([H])O[*:4] c([H])c1[H] 53.[H]Oc1c([H])c([H])c(C([H]) [H][*:2]•[H][*:2] [H][*:3] [H]C([H]) [H][*:5][H][*:6] ([H])[C@](O[H])(C(═O)OC([H]) ([H])O[*:4]([H])[*:1])[*:1])c([H]) c1OC([H])([H])[H]•[H][*:1] 54.[H]Oc1c([H])c([H])c([C@] O═[*:2] [H][*:3] [H]C([H]) [H]Oc1c([H])c([H])[H]O[*:6] ([H])(O[*:5])[*:1])c([H])c1[H] ([H])O[*:4] c([C@]([H])[H][*:1]•[H][*:1] (O[*:5])[*:1]) c([H])c1[H] 55. [H]Oc1c([H])c([C@]([H])[H][*:2]•[H][*:2] [H][*:3] [H]C([H]) [H][*:5] [H]Oc1c([H])c([C@](O[*:6])[*:1])c([H])c([H]) ([H])[*:4] ([H])(O[*:6])[*:1])c1OC([H])([H])[H]•[H][*:1]•[H] c([H])c([H])c1OC([H]) [*:1] ([H])[H] 56.[H]OC([H])([H])C([H])([H]) [H]OC([H])([H])C([H])([H]) [H][*:3] [H][*:4][H][*:5] [H]O[*:6] c1c(OC([H])([H])[H])c([H]) c1c(OC([H])([H])[H])c([H])c([H])c(C([H])([H])[*:1]) c([H])c(C([H])([H])[*:1])c1O[*:2]•[H][*:1]•[H][*:1] c1O[*:2]•[H][*:2] 57.[H]Oc1c([H])c([C@@]([H]) [H][*:2]•[H][*:2] [H][*:3] [H]C([H]) [H][*:5][H]Oc1c([H])c([C@@] (O[*:6])[*:1])c([H])c([H]) ([H])[*:4]([H])(O[*:6])[*:1]) c1OC([H])([H])[H]•[H][*:1]•[H] c([H])c([H])c1OC([H])[*:1] ([H])[H] 58. [H]Oc1c([H])c([H])c([C@] [H][*:2]•[H][*:2] [H][*:3][H]C([H]) [H][*:5] [H]Oc1c([H])c([H]) ([H])(O[*:6])[*:1])c([H])([H])[*:4] c([C@]([H])(O[*:6]) c1OC([H])([H])[H]•[H][*:1]•[H][*:1])c([H])c1OC([H]) [*:1] ([H])[H]

Tab1e 1-C R1 R2 R3 R4 R5 1. [H]Oc1c(OC([H]) [H][*:2] [H]O[*:3][H]Oc1c(OC([H])([H]) [H]C([H])([H])[*:5] ([H])[H])c([H])c(C[H])c([H])c(C([H])([H]) ([H])([H])C([H])═C C([H])═C([H])[H])c([H])([H])[H])c([H])c1 c1C([H])([H])/C([H])═C C([H])([H])/C([H])═C(\[H])Oc(c([H]):[*:4] (\[H])Oc(c([H]): [*:4]):[*:1].[H][*:1] 2.[H]C([H])([H])Oc [H][*:2] [H]O[*:3] [H]C([H])([H])Oc(c(OC[H]C([H])([H])[*:5] (c(OC([H])([H])[H]): ([H])([H])[H]):[*:4]):[*:4]):[*:1].[H]O [*:1] c1c([H])c([H])c([C @@]([H])(C([H])═C([H])[H])[*:1])c ([H])c1[H] 3. [H]C([H])([H])Oc [H][*:2] [H]O[*:3][H]C([H])([H])Oc(c(OC [H]C([H])([H])[*:5] (c(OC([H])([H])[H]):([H])([H])[H]):[*:4]): [*:4]):[*:1].[H]O [*:1] c1c([H])c([H])c([C@]([H])(C([H])═C ([H])[H])[*:1])c ([H])c1[H] 4. [H]C([H])([H])Oc[H][*:2] [H]O[*:3] [H]C([H])([H])Oc(c(OC [H]C([H])([H])[*:5](c(OC([H])([H])[H]): ([H])([H])[H]):[*:4]): [*:4]):[*:1].[H]O [*:1]c1c([H])c([H])c([H]) c([H])c1/C([H])═C (/[H])C([H])([H]) [*:1] 5.[H]Oc1c([H])c([H]) [H][*:2] [H]O[*:3] [H]c(c(OC([H])([H])[H]C([H])([H])[*:5] c([H])c([C@]([H]) [H]):[*:1]):[*:4](C([H])═C([H])[H]) [*:1])c1[H].[H]c(c (OC([H])([H])[H]): [*: 1]):[*:4]6. [H]Oc(c([H]):[*:1]): [H][*:2] [H]O[*:3] [H]Oc(c([H]):[*:1]):[H]C([H])([H])[*:5] [*:4].[H]Oc1c([H]) [*:4] c(O[H])c2c(c1[H])O[C@@]([H])([*:1]) [C@]([H])(O[H])C2 ([H])[H] 7. [H]C([H])([H])O[*:[H][*:2] [H]Oc(c(OC([H])([H]) [H]Oc1c([H])c(O[H])c [H]Oc1c([H])c(O[H])c1].[H]Oc(c(OC([H]) [H])c([H]):[*:3]):[*:1] (C(═O)C([H])([H])[*:4])(C(═O)C([H])([H])[*: ([H])[H])c([H]): c([*:5])c1[H].[H][*:4]4])c([*:5])c1[H] [*:3]):[*:1] 8. [H]O[*:1].[H]Oc(c [H][*:2][H]Oc(c(OC([H])([H]) [H]Oc1c([H])c(O[H])c [H]Oc1c([H])c(O[H])c(OC([H])([H])[H]): [H]):[*:1])c([H]):[*:3] (C([H])([H])[C@]([H])(C([H])([H])[C@]([H]) [*:1])c([H]):[*:3] (O[H])[*:4])c([*:5])c1(O[H])[*:4])c([*:5])c [H].[H][*:4] 1[H] 9. [H]C([H])([H])O[*: [H][*:2][H]Oc(c([H])c([H]):[*: [H]Oc1c([H])c(O[H])c [H]Oc1c([H])c(O[H])c1].[H]Oc(c([H])c 3]):[*:1] (C([H])([H])[C@@]([H]) (C([H])([H])[C@@]([H]):[*:3]):[*:1] (O[H])[*:4])c([*:5])c1 ([H])(O[H])[*:4])c[H].[H][*:4] ([*:5])c1[H] 10. [H]C([H])([H])O[*: [H][*:2][H]Oc(c([H])c([H]):[*: [H]Oc1c([H])c(OC([H]) [H]Oc1c([H])c(OC([H])1].[H]Oc(c([H])c 3]):[*:1] ([H])[H])c(C([H])([H]) ([H])[H])c(C([H])([H]):[*:3]):[*:1] [C@@]([H])(O[H])[*:4]) ([H])[C@@]([H])(O[H])c([*:5])c1[H].[H][*:4] [*:4])c([*:5])c1[H] 11. [H]O[*:1].[H]Oc(c[H][*:2] [H]Oc(c(OC([H])([H]) [H]Oc1c([H])c(O[H])c [H]Oc1c([H])c(O[H])c(OC([H])([H])[H]): [H]):[*:1])c([H]):[*:3] (C([H])([H])[C@]([H])(C([H])([H])[C@]([H]) [*:1])c([H]):[*:3] (O[H])[*:4])c([*:5])c1(O[H])[*:4])c([*:5])c [H].[H][*:4] 1[H] 12. [H]C([H])([H])O[*: [H][*:2][H]Oc(c([H])c([H]):[*: [H]Oc1c([H])c(O[H])c [H]Oc1c([H])c(O[H])c1].[H]Oc(c([H])c 3]):[*:1] (C([H])([H])[C@]([H]) (C([H])([H])[C@]([H])([H]):[*:3]):[*:1] (O[H])[*:4])c([*:5])c1 (O[H])[*:4])c([*:5])c[H].[H][*:4] 1[H] 13. [H]O[*:1].[H]Oc(c [H][*:2] [H]Oc(c(OC([H])([H])[H]Oc1c([H])c(O[H])c [H]Oc1c([H])c(O[H])c (OC([H])([H])[H]):[H]):[*:1])c([H]):[*:3] (C([H])([H])[C@@]([H]) (C([H])([H])[C@@]([H])[*:1])c([H]):[*:3] (O[H])[*:4])c([*:5])c1 (O[H])[*:4])c([*:5])[H].[H][*:4] c1[H] 14. [H]C([H])([H])O[*: [H][*:2][H]Oc(c([H])c([H]):[*: [H]Oc1c([H])c(O[H])c [H]Oc1c([H])c(O[H])c1].[H]Oc(c([H])c 3]):[*:1] (C([H])([H])[C@@]([H]) (C([H])([H])[C@@]([H])([H]):[*:3]):[*:1] (O[H])[*:4])c([*:5])c1 (O[H])[*:4])c([*:5])[H].[H][*:4] c1[H] 15. [H]C([H])([H])O[*: [H][*:2] [H]Oc(c(O[H]):[*:1])c[H]Oc1c([H])c(O[H])c [H]Oc1c([H])c(O[H])c 1].[H]Oc(c(O[H]): ([H]):[*:3](C(═O)C([H])([H])[*:4]) (C(═O)C([H])([H])[*: [*:1])c([H]):[*:3]c([*:51)c1[H].[H][*:4] 4])c([*:5])c1[H] 16. [H]O[*:1].[H]Oc1c [H][*:2][H]Oc1c([H])c(O[H])c [H]Oc1c([H])c(O[H])c [H]Oc1c([H])c(O[H])c([H])c(O[H])c(C([H]) (C([H])([H])[C@]([H]) (C([H])([H])[C@]([H])(C([H])([H])[C@]([H]) ([H])[C@]([H]) (OC(c(c(O[H])c(OC([H])(OC(c(c(O[H])c(OC([H]) (OC(c(c(O[H])c(OC (OC(c(c(O[H])c(O([H])[H]):[*:1]):[*: ([H])[H]):[*:1]):[*:3]) ([H])([H])[H]):[*:C([H])([H])[H]):[*: 3])(C([H])([H])[H])C (C([H])([H])[H])C([H])1]):[*:3])(C([H]) 1]):[*:3])(C([H])([H]) ([H])([H])[H])[*:4])c([H])[H])[*:4])c([*:5])c1 ([H])[H])C([H])([H]) [H])C([H])([H])([*:5])c1[H] [H].[H][*:4] [H])[*:4])c([*:5]) [H])[*:4])c([*:5]) c1[H]c1[H] 17. [H]O[*:1].[H]Oc(c [H][*:2] [H]Oc(c([H]):[*:1])c[H]Oc1c([H])c([*:5])c [H]Oc1c([H])c([*:5])c ([H]):[*:1])c([H]):([H]):[*:3] (C(═O)C([H])([H])[*:4]) (C(═O)C([H])([H])[*: [*:3]c(O[H])c1C([H])([H]) 4])c(O[H])c1C([H]) [H].[H][*:4] ([H])[H] 18.[H]O[*:1].[H]Oc(c [H][*:2] [H]Oc(c([H]):[*:1])c [H]Oc1c([H])c(O[H])c[H]Oc1c([H])c(O[H])c ([H]):[*:1])c([H]): ([H]):[*:3](C([H])([H])[C@]([H]) (C([H])([H])[C@] [*:3] (O[H])[*:4])c([*:5])c1([H])(O[H])[*:4])c [H].[H][*:4] ([*:5])c1[H] 19. [H]O[*:1].[H]Oc(c[H][*:2] [H]Oc(c(OC([H])([H]) [H]Oc1c([H])c(O[H])c [H]Oc1c([H])c(O[H])c(OC([H])([H])[H]): [H]):[*:1])c([H]):[*:3] (C(═O)[C@]([H])(O[H])(C(═O)[C@]([H])(O [*:1])c([H]):[*:3] [*:4])c([*:5])c1[H].[H][[H])[*:4])c([*:5]) *:4] c1[H] 20. 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[H]Oc(c(OC([H])([H]) [H][*:2][H]Oc(c(OC([H])([H]) [H]Oc1c([H])c([H])c(C [H]Oc1c([H])c([H])c[H])c(OC([H])([H]) [H])c(OC([H])([H]) ([H])([H])C([H])([H])[*:(C([H])([H])C([H])([H]) [H]):[*:3]):[*: [H]):[*:3]):[*:1]4])c([*:5])c1[H].[H][*:4] [*:4])c([*:5])c1[H] 1].[H][*:1] 56.[H]Oc(c(OC([H])([H]) [H][*:2] [H][*:3] [H]Oc(c(OC([H])([H])[[H]C([H])([H])[*:5] [H]):[*:1]):[*:4]. H]):[*:1]):[*:4][H]Oc1c([H])c([H]) c2c(c1[H])OC([H]) ([H])[C@@]([H]) ([*:1])C2([H])[H]57. [H]O[*:1].[H]Oc1c [H][*:2] [H]O[*:3] [H]Oc1c([H])c([H])c2c[H]C([H])([H])[*:5] ([H])c([H])c2c(c1[H]) (c1[H])OC([H])([H])[COC([H])([H])[C@]([H]) @]([H])(c(c([H]):[*:4]): (c(c([H]):[*:4]):[*:1])C2═O [*:1])C2═O 58. [H]Oc(c([H]):[*:4]): [H][*:2][H]Oc1c([H])c([C@] [H]Oc(c([H]):[*:4]): [H]Oc1c([H])c([C@]([H])[*:1].[H][*:1] ([H])(C(═O)[*:3])C([H]) [*:1] (C(═O)[*:3])C([H])([H])[*:5])c(OC([H]) ([H])[*:5])c(OC([H]) ([H])[H])c([H])c1OC([H])[H])c([H])c1OC ([H])([H])[H] ([H])([H])[H] 59. [H]Oc1c([H])c([H])[H][*:2] [H]O[*:3] [H]Oc1c([H])c([H])c(C [H]C([H])([H])[*:5]c(C([H])([H])[C ([H])([H])[C@@]([H]) @@]([H])(N([H])(N([H])C([H])([H])C([H]) C([H])([H])C([H]) ([H])c(c(OC([H])([H])([H])c(c(OC([H])([H]) [H]):[*:4]):[*:1])[*:1])c [H]):[*:4]):[*:1])([H])c1[H] [*:1])c([H])c1[H] 60. [H]C([H])([H])O[*: [H][*:2][H]Oc1c([H])c(OC([H]) [H]Oc(c([H]):[*:4]): [H]Oc1c([H])c(OC([H])1].[H]Oc(c([H]):[ ([H])[H])c([H])c([H]) [*:1] ([H])[H])c([H])c([H])c1[C@@]([H])(C([H]) c1[C@@]([H])(C([H]) ([H])[*:3])C([H])([H])[*:3])C([H])([H]) ([H])[*:5] [*:5] 61. [H]Oc(c([H])c([H]): [H][*:2][H]Oc(c([H])c([H]):[*: [H]Oc1c(C([H])([H]) [H]Oc1c(C([H])([H])[*:3]):[*:1].[H][* 3]):[*:1] [H])c(OC([H])([H])[H])c[H])c(OC([H])([H])[H]) :1] ([H])c([*:5])c1C([H]) c([H])c([*:5])c1C([H])([H])C([H])([H])[*:4].[H][*: ([H])C([H])([H])[*:4] 4] 62.[H]Oc1c([H])c([H]) [H][*:2] [H]C([H])([H])O[*:3] [H]Oc1c([H])c([H])c[H][*:5] c([H])c(C([H])([H]) ([H])c(C([H])([H])[C@@][C@@]2([H])c(:[*:1]) 2([H])c(:[*:1])c(:[*:4]) c(:[*:4])C([H])C([H])([H])[N+]([H]) ([H])[N+]([H])(C (C([H])([H])[H])C2([H])([H])([H])[H])C2([H]) [H])c1OC([H])([H])[H] [H])c1OC([H])([H])[H].[H][*:1] 63. [H]C([H])([H])O[*: [H][*:2] [H]Oc(c([H])c([H]):[*:[H]Oc1c([H])c([*:5])c [H]Oc1c([H])c([*:5])c 1].[H]Oc(c([H])c 3]):[*:1](C([H])([H])C([H])([H]) (C([H])([H])C([H])([H]) ([H]):[*:3]):[*:1][*:4])c([H])c1OC([H]) [*:4])c([H])c1OC([H]) ([H])[H].[H][*:4] ([H])[H]64. [H]C([H])([H])O[*: [H][*:2] [H]Oc(c([H])c([H]):[*:[H]Oc1c([H])c([*:5])c [H]Oc1c([H])c([*:5])c 1].[H]Oc(c([H])c 3]):[*:1](C([H])([H])C([H])([H]) (C([H])([H])C([H])([H]) ([H]):[*:3]):[*:1][*:4])c([H])c1OC([H]) [*:4])c([H])c1OC([H]) ([H])[H].[H][*:4] ([H])[H]65. [H]Oc1c(OC([H])([H]) [H][*:2] [H]C([H])([H])O[*:3][H]Oc1c(OC([H])([H]) [H][*:5] [H])c([H])c([H]) [H])c([H])c([H])c([H])c1c([H])c1C([H])([H]) C([H])([H])[C@@]1([H]) [C@@]1([H])cc(:[*:1])c(:[*:4])C([H]) (:[*:1])c(:[*:4])C ([H])[N+]([H])(C([H])([H])([H])[N+]([H]) ([H])[H])C1([H])[H] (C([H])([H])[H])C1([H])[H].[H][*:1] 66. [H]Oc1c([H])c([H]) [H][*:2] [H]C([H])([H])O[*:3][H]Oc1c([H])c([H])c [H][*:5] c([H])c(C([H])([H]) ([H])c(C([H])([H])[C@]2[C@]2([H])c(:[*: ([H])c(:[*:1])c(:[*:4])C 1])c(:[*:4])C([H])([H])([H])[N+]([H])(C ([H])[N+]([H])(C([H]) ([H])([H])[H])C2([H])([H])[H])C2([H]) [H])c1OC([H])([H])[H] [H])c1OC([H])([H]) [H].[H][*:1]67. [H]Oc1c([H])c2c(c [H][*:2] [H]O[*:3] [H]Oc1c([H])c2c(c([H])[H]C([H])([H])[*:5] ([H])c1OC([H])([H]) c1OC([H])([H])[H])C[H])C([H])([H])[N+] ([H])([H])[N+]([H])(C ([H])(C([H])([H])C([H])([H])C([H])([H])c(c ([H])([H])c(c ([H]):[*:4]):[*:1])[C@@]([H]):[*:4]):[*:1]) ([H])([*:1])C2([H])[H] [C@@]([H])([*:1]) C2([H])[H]68. [H]Oc1c([H])c([H]) [H][*:2] [H][*:3] [H]Oc1c([H])c([H])c(N[H]C([H])([H])[*:5] c(N([H])[C@@]([H]) ([H])[C@@]([H])(OC (OC(═O)c(c(O(═O)c(c(OC([H])([H]) C([H])([H])[H]):[*: [H]):[*:4]):[*:1])[*:1])c4]):[*:1])[*:1])c ([H])c1[H] ([H])c1[H] 69. [H]Oc1c([H])c([H]) [H][*:2][H]O[*:3] [H]Oc1c([H])c([H])c2c [H]C([H])([H])[*:5] c2c(c1[H])OC([H])(c1[H])OC([H])([H])[C ([H])[C@@](O[H]) @@](O[H])(C([H])([H])(C([H])([H])c(c c(c([H]):[*:4]):[*:1])[C ([H]):[*:4]):[*:1])@@]2([H])[*:1] [C@@]2([H])[*:1] 70. [H]Oc1c([H])c([H]) [H][*:2][H]O[*:3] [H]Oc1c([H])c([H])c2c [H]C([H])([H])[*:5] c2c(c1[H])OC([H])(c1[H])OC([H])([H])[C ([H])[C@](O[H]) @](O[H])(C([H])([H])c(C([H])([H])c(c([H]): (c([H]):[*:4]):[*:1]) [*:4]):[*:1])[C@]2[C@]2([H])[*:1] ([H])[*:1] 71. [H]Oc(c([H]):[*:1]): [H][*:2] [H][*:3][H]Oc(c([H]):[*:1]): [H]C([H])([H])[*:5] [*:4].[H]Oc1c(O [*:4]C([H])([H])[H])c([H])c ([H])c2c1C([H])([H]) [N+]([H])([H])C([H])([H])[C@@]2([H])[*:1] 72. [H]O[*:1].[H]Oc(c [H][*:2] [H]O[*:3][H]Oc(c([H]):[*:1]): [H]C([H])([H])[*:5] ([H]):[*:1]):[*:4] [*:4] 73.[H][*:1].[H]c(c(O [H]Oc1c([H])c([C@ [H]Oc1c([H])c([C@@][H]c(c(OC([H])([H]) [H][*:5] C([H])([H])[H]): @]([H])(C([H])([H])[H])(C([H])([H])[N+] [H]):[*:4]):[*:1] [*:4]):[*:1] [N+]([H])([H])C([H])([H])([H])C([H])([H]) ([H])[*:3])[*:2])c([H]) [*:3])[*:2])c([H])c([H])c([H])c1OC([H])([H])[H] c1OC([H])([H])[H] 74. [H][*:1].[H]c(c(O[H]Oc1c([H])c([H])c [H]Oc1c([H])c([H])c [H]c(c(OC([H])([H]) [H][*:5]C([H])([H])[H]): ([C@@]([H])(C([H]) ([C@@]([H])(C([H]) [H]):[*:4]):[*:1][*:4]):[*:1] ([H])N([H])C([H]) ([H])N([H])C([H])([H]) ([H])[*:3])[*:2])c[*:3])[*:2])c([H])c1O[H] ([H])c1O[H] 75. [H][*:1].[H]c(c(O[H]Oc1c([H])c([H])c [H]Oc1c([H])c([H])c [H]c(c(OC([H])([H]) [H][*:5]C([H])([H])[H]): ([C@]([H])(C([H])([H]) ([C@]([H])(C([H])([H])[H]):[*:4]):[*:1] [*:4]):[*:1] N([H])C([H])([H])[*: N([H])C([H])([H])[*:3])[*:2])c([H])c1O[H] 3])[*:2])c([H])c1O[H] 76. [H]Oc(c([H]):[*:4]):[H]C([H])([H])C(O[*: [H]C([H])([H])C(O[*: [H]Oc(c([H]):[*:4]): [H][*:5][*:1].[H][*:1] 2])(C([H])([H])[H]) 2])(C([H])([H])[H])C [*:1]C([H])([H])C(═O)[*:3] ([H])([H])C(═O)[*:3] 77. [H]Oc1c([H])c2c(c[H][*:2] [H]O[*:3] [H]Oc1c([H])c2c(c([H]) [H]C([H])([H])[*:5]([H])c1OC([H])([H]) c1OC([H])([H])[H])C [H])C([H])([H])[N+]([H])([H])[N+]([H])(C ([H])(C([H])([H])c ([H])([H])c(c([H]):[*:4]):(c([H]):[*:4]):[*: [*:1])C([H])([H])C2([H]) 1])C([H])([H]) [*:1]O2([H])[*:1] 78. [H][*:1].[H]c(c(O [H]Oc1c(OC([H])([H])[H]Oc1c(OC([H])([H]) [H]c(c(OC([H])([H]) [H][*:5] C([H])([H])[H]):[H])c([H])c([H])c2 [H])c([H])c([H])c2c1 [H]):[*:4]):[*:1] [*:4]):[*:1]c1C([H])([H])[N+]([H]) C([H])([H])[N+]([H]) (C([H])([H])[*:3])(C([H])([H])[*:3])C C([H])([H])C2([H])[*:2] ([H])([H])C2([H])[*:2] 79.[H]Oc(c([H]):[*:1]): [H]Oc1c([H])c2c(c([H]) [H][*:3][H]Oc(c([H]):[*:1]): [H]C([H])([H])[*:5] [*:4].[H][*:1]c1OC([H])([H])[H]) [*:4] [C@]([H])([*:2]) C([H])([H])[N+]([H])([H])C2([H])[H] 80. [H]c(n:[*:1])n([H]) [H]c(n:[*:1])n([H])c[H]n(n:[*:1]):[*:3] O═[*:4] c(═O):[*:2].[H]n(n: (═O):[*:2] [*:1]):[*:3]81. [H]Oc(c([H])c([C [H][*:2].[H][*:2] [H]Oc(c([H])c([C@]([H]) O═[*:4][H]C([H])([H])[*:5] @]([H])(c1c([H])c (c1c([H])c([H])c(O([H])c(OC([H])([H]) C([H])([H])[H])c(OC [H])c(OC([H])([H])([H])([H])[H])c1[H])[N+] [H])c1[H])[N+] ([H])([H])[*:3]):[*:1])([H])([H])[*:3]):[*: c(O[H])c([H]):[*:1].[H] 1])c(O[H])c([H]): [*:3][*:1] 82. [H]Oc(c([H]):[*:1]): [H]Oc1c([H])c2c(c [H][*:3][H]Oc(c([H]):[*:1]): [*:4].[H][*:1] ([H])c1OC([H])([H]) [*:4][H])[C@@]([H])([*:2]) C([H])([H])[N+]([H]) ([H])C2([H])[H] 83.[H]Oc(c([H])c([C [H][*:2].[H][*:2] [H]Oc(c([H])c([C@@] O═[*:4][H]C([H])([H])[*:5] @@]([H])(c1c([H]) ([H])(c1c([H])c([H])cc([H])c(OC([H])([H]) (OC([H])([H])[H])c(O [H])c(OC([H])([H])C([H])([H])[H])c1[H]) [H])c1[H])[N+]([H]) [N+]([H])([H])[*:3]):([H])[*:3]):[*:1]) [*:1])c(O[H])c([H]):[*: c(O[H])c([H]) 1].[H][*:3] 84.[H]Oc1c([H])c2c(c [H][*:2] [H][*:3] [H]c(c(OC([H])([H]) ([H])c1O[H])[C@][H]):[*:4]):[*:1] ([H])([*:1])[N+] ([H])([H])[C@]([H])(C(═O)[O-])C2([H]) [H].[H]c(c(OC([H]) ([H])[H]):[*:4]): [*:1] 85.O═[*:1] [H]Oc1c([H])c([H])c [H]Oc1c([H])c([H])c [H][*:4].[H][*:4][H]C([H])([H])[*:5] ([C@]([H])(c2c([H]) ([C@]([H])(c2c([H])c(Oc(O[H])c(OC([H])([H]) [H])c(OC([H])([H])[H]) [H])c([H])c2C([H])c([H])c2C([H])([H])[*: ([H])[*:2])[*:3])c 2])[*:3])c([H])c1OC([H])c1OC([H])([H]) ([H])([H])[H].[H][*:3] [H].[H][*:2] 86.[H]Oc1c([H])c2c(c [H][*:2] [H]O[*:3] [H]Oc1c([H])c2c(c([H])([H])c1OC([H])([H]) c1OC([H])([H])[H])C [H])C([H])(c(c([H]):([H])(c(c([H]):[*:4]):[*:1]) [*:4]):[*:1])C C([H])([H])[N+]([H1)([H])([H])[N+]([H]) (C([H])([H])[*:1])C2 (C([H])([H])[*:1]) ([H])[H]C2([H])[H]

TABLE 1-D R1 R2 R3 R4 R5 R6 1. O═[*:1]•[H]c1c([H]) [H][*:2] [H][*:3][H][*:4] [H]c1c([H])c([H]) [H][*:6] c([H])c(N([H])C(═O)C([H])c(N([H])C(═O) ([H])C([H])([H])C([H]) C([H])([H])([H])n(c([H])n:[*:5]):[*:1]) C([H])([H])C([H]) c(C(═O)N([H])[H])c1[H]([H])n(c([H]) n:[*:5]):[*:1]) c(C(═O)N([H]) [H])c1[H] 2.O═[*:1]•[H]c1c([H]) [H]C([H])([H]) [H]C([H])([H]) [H][*:4] [H]c1c([H])[H][*:6] c(N([H])C(═O)C([H])([H]) O[*:2] O[*:3] c(N([H])C(═O)C([H])C([H])([H])n(c([H]) ([H])C([H]) n:[*:5]):[*:1])c([H])c([H])([H])n(c([H]) c1C(═O)N([H])[H] n:[*:5]):[*:1]) c([H])c([H])c1C(═O)N([H])[H] 3. O═[*:1]•[H]c1c([H]) [H][*:2] [H][*:3][H]c1c([H])c([H]) [H][*:5] [H][*:6] c([H])c(N([H])C(═O)C([H])c(N([H])C(═O)C([H]) ([H])n(c([H])n:[*:4]):[*:1]) ([H])n(c([H])c(C(═O)N([H])[H])c1[H] n:[*:4]):[*:1])c(C(═O) N([H])[H])c1[H] 4.[H]C([H])(C(═O)O[*:4]) [H]Oc1c([H]) [H]Oc1c([H]) [H]C([H])(C(═O)[H]O[*:5] [H][*:6] [*:1]•[H]Oc1c([H])c([H]) c([C@@]([H]) c([C@@]O[*:4])[*:1] c([*:1])c([H])c1OC([H]) (O[*:2])[C@@] ([H])(O[*:2])([H])[H]•[H][*:1] ([H])(O[H]) [C@@]([H]) C([H])([H])[*:3])(O[H])C([H])([H]) c([H])c(O[H]) [*:3])c([H])c(O[H]) c1OC([H])([H])[H]c1OC([H])([H])[H] 5. [H]OC([H])([H])[*:1]•[H] [H][*:2] [H]O[*:3][H]Oc1c([H])c([H]) [H]Oc1c([H]) [H][*:6] Oc1c([H])c([H])c([C@]c([C@]([H])(O[*:4]) c(O[H])c2c(c1[H]) ([H])(O[*:4])[*:1])c([H])[*:1])c([H])c1OC([H]) O[C@@]([H]) c1OC([H])([H])[H]•[H][*:1] ([H])[H]([*:5])C([H])([H]) C2═O 6. [H]Oc1c([H])c(O[H]) [H]Oc1c([H])[H]Oc1c([H])c([H]) [H][*:4] [H][*:5] [H][*:6] c(C(═O)[C@]([H])(O[H])c([H])c([C@@] c([C@@]([H]) [*:1])c(O[*:1])c1[H]•[H] ([H])(O[*:3])(O[*:3])[C@@] [*:1] [C@@]([H]) ([H])(O[*:2])C([H]) (O[*:2])C([H])([H])O[H])c([H]) ([H])O[H])c([H]) c1OC([H])([H])[H] c1OC([H])([H])[H] 7.O═[*:1]•[H]c1c([H]) [H][*:2] [H][*:3] [H]c1c([H])c([H]) [H][*:5][H][*:6] c([H])c(N([H])C(═O)C([H]) c(N([H])C(═O)C([H])([H])N([H])C(═O)C([H]) ([H])N([H])C(═O) ([H])n(c([H])n:[*:4]):[*:1])C([H])([H])n(c([H]) c(C(═O)N([H])[H])c1[H] n:[*:4]):[*:1])c(C(═O)N([H])[H])c1[H] 8. [H]C([H])(C(═O)O[*:5]) [H]O[*:2] [H][*:3][H]Oc1c([H])c([H]) [H]C([H])(C(═O) [H][*:6] [*:1]•[H]Oc1c([H])c([H])c(/C([H])═C(/[H]) O[*:5])[*:1] c([*:1])c([H])c1OC([H])[*:4])c([H])c1OC([H]) ([H])[H]•[H][*:1] ([H])[H] 9.[H]Oc1c([H])c([H])c([H]) [H]O[*:2] [H]C([H])([H]) [H][*:4] [H][*:5][H][*:6] c(C([H])([H])[C@@] O[*:3] ([H])(C(═O)C([H])([H])C([H])([H])c2c([H]) c(O[H])c(O[H])c(OC([H]) ([H])[H])c2[H])[C@]([H])(O[H])C([H])([H]) [*:1])c1[H]•[H][*:1]•[H] [*:1] 10.O═[*:1]•[H]c1c([H])c([H]) [H]O[*:2] [H]C([H])([H]) [H]c1c([H])c([H])[H][*:5] [H][*:6] c2sc(-c(c(o:[*:4])N([H]) C1(C([H])([H])c2sc(-c(c(o:[*:4])N([H]) [H]):[*:1])nc2c1[H] [H])C([H])([H])[H]):[*:1])nc2c1[H] [C@@]2([H]) C([H])([H])[C@@] (C([H])([H])[H])(C1([H])[H])C([H]) ([H])[N+]2([H]) C([H])([H])[*:3] 11.[H]OC(═C(/[H])C(═O) [H]C([H])([H]) [H]C([H])([H]) [H][*:4] [H][*:5][H][*:6] [C@]([H])([C@@]([H]) O[*:2] O[*:3] (c1c([H])c([H])c(O[H])c(OC([H])([H])[H])c1[H]) C([H])([H])C([H])═C([H])[*:1])[*:1])/C([H])═C(\[H]) c1c([H])c([H])c(O[H]) c(OC ([H])([H])[H])c1[H]•[H][*:1] 12. [H][*:1]•[H][*:1]•[H] [H]C([H])([H]) [H][*:3][H]c1c([H])c(N([H]) [H][*:5] [H]C([H]) c1c([H])c(N([H])c2nc(═O) O[*:2]c2nc(═O)n(C([H])([H]) ([H])O[*:6] n(C([H])([H])[*:1])c([*:4])[*:1])c([*:4])c2[H]) c2[H])c([H])c([H]) c([H])c([H])c1C(═O) c1C(═O)[O—][O—] 13. O═[*:1]•[H]c1c(OC([H]) [H][*:2] [H][*:3] [H]c1c(OC([H])([H])[H][*:5] [H][*:6] ([H])[H])c(OC([H])([H]) [H])c(OC([H])([H])[H])c(OC([H])([H])[H]) [H])c(OC([H])([H]) c([H])c1N([H])C(═O)[H])c([H])c1N([H]) C([H])([H])[C@@] C(═O)C([H])([H])([H])(C(═O)N([H])[*:4]) [C@@]([H]) N([H])[*:1] (C(═O)N([H])[*:4])N([H])[*:1] 14. [H][*:1]•[H][*:1]•[H] [H]C([H])([H]) [H]C([H])([H])[H][*:4] [H][*:5] [H][*:6] c1c([H])c([H])n2c(═O) O[*:2] O[*:3]c3c([H])c(C(═O)N([H])C ([H])([H])[*:1])c(N([H]) [H])[n+](C([H])([H])C([H])([H]) C([H])([H])OC([H]) ([H])[H])c3nc2c1[H] 15.[H]Oc1c([H])c(O[H]) [H]O[*:2] [H][*:3] [H][*:4] [H]Oc1c([H])c([H])[H]Oc1c([H]) c(C(═O)[C@@]([H]) c([C@]([H]) c([H])c([C@](O[H])[*:1])c(O[*:1]) (O[*:6])[C@@] ([H])(O[*:6]) c1[H]•[H][*:1]([H])(C([H]) [C@@]([H]) ([H])O[H])[*:5]) (C([H])([H]) c([H])c1OC([H])O[H])[*:5]) ([H])[H] c([H])c1OC([H]) ([H])[H] 16. [H][*:1]•[H][*:1]•[H][H][*:2] [H]C([H])([H]) [H]O[*:4] [H]c1c([H])c([H]) [H]c1c([H])c([H])c1c([H])c2n(c(═O)c1[H]) C([H])([H])[*:3] c2c(nc(-c(c(o:[*:5])c2c(nc(-c(c(o:[*:5]) C([H])([H])[C@@]1([H]) C([H])([H])[H])C([H])([H])[H]) C([H])([H])[C@]2([H]) c(═O):[*:6])n2C([H]) c(═O):[*:6])C([H])([H])[N+]([H]) ([H])[H])c1[H] n2C([H])([H]) ([*:1])C1([H])[H][H])c1[H] 17. O═[*:1]•[H]C1([H]) [H][*:2] [H][*:3] [H]C1([H])c(n:[*:4])[H][*:5] [H]c1c([H]) c(n:[*:4])n(:[*:1])C([H]) n(:[*:1])C([H])([H])c(N([H])C(═O) ([H])C1([H])[H] C1([H])[H] C([H])([H]) O[*:6])c([H])c([H])c1C(═O) N([H])[H] 18. O═[*:1]•[H]c1nc([H]) [H]C([H])([H])[H]C([H])([H]) [H][*:4] [H]c1nc([H]) [H][*:6] c(C(═O)N([H])C([H])([H])O[*:2] O[*:3] c(C(═O)N([H])C([H]) C([H])([H])n(c(n:[*:5])([H])C([H])([H]) C([H])([H])C([H])([H]) n(c(n:[*:5])C([H])[H]):[*:1])c([H])c1[H] ([H])C([H])([H]) [H]):[*:1])c([H]) c1[H] 19.[H][*:1]•[H][*:1]•[H] [H]C([H])([H]) [H]C([H])([H]) [H][*:4] [H][*:5][H][*:6] c1c([H])c([H])n2c(═O) O[*:2] O[*:3] c3c([H])c(C(═O)N([H])C([H]) ([H])C([H]) ([H])C([H])([H])OC([H]) ([H])[H])c(N([H])[H])[n+](C([H])([H])[*:1]) c3nc2c1[H] 20. [H][*:1]•[H][*:1]•[H][H]C([H])([H]) [H][*:3] [H][*:4] [H][*:5] [H][*:6] c1c([H])c([H])n2c(═O)O[*:2] c3c([H])c(C(═O)N([H])[*:1]) c(N([H])[H])[n+](C([H])(C([H])([H])[H])C([H]) ([H])[H])c3nc2c1[H] 21. [H][*:1]•[H][*:1]•[H][H]C([H])([H]) [H][*:3] [H][*:4] [H][*:5] [H][*:6] c1c([H])c([H])n2c(═O)O[*:2] c3c([H])c(C(═O)N([H]) C([H])([H])[*:1]) c(N([H])[H])[n+](C([H])(C([H])([H]) [H])C([H])([H])[H]) c3nc2c1[H] 22.[H][*:1]•[H][*:1]•[H] [H]C([H]) [H]C([H])(O[*:2]) [H][*:4] [H][*:5][H][*:6] c1c([H])c([H])n2c(═O) (O[*:2])O[*:3] O[*:3] c3c([H])c(C(═O)N([H]) [*:1]) c(N([H])[H])[n+] (C([H])([H])C([H])([H])[H])c3nc2c1[H] 23. O═[*:1]•[H]c1c([H]) [H]C([H])([H]) [H]C([H])([H])[H][*:4] [H]c1c([H]) [H][*:6] c(N([H])C(═O)C([H])([H]) O[*:2] O[*:3]c(N([H])C(═O) C([H])([H])n(c([H]) C([H])([H])C([H])n:[*:5]):[*:1])c([H])c([H]) ([H])n(c([H]) c1C(═O)OC([H])([H])[H]n:[*:5]):[*:1]) c([H])c([H])c1C(═O) OC([H])([H])[H] 24.O═[*:1]•[H]c1c([H]) [H][*:2] [H][*:3] [H]c1c([H])c(N([H]) [H][*:5][H][*:6] c(N([H])C(═O)C([H])([H]) C(═O)C([H])([H]) C([H])([H])n(c([H])C([H])([H])n(c([H]) n:[*:4]):[*:1])c([H]) n:[*:4]):[*:1])c([H])c2c1C(═O)OC2([H])[H] c2c1C(═O)OC2([H])[H] 25. [H][*:1]•[H][*:1]•[H][H]C([H])([H]) [H][*:3] [H]c1c([H])c(N([H]) [H][*:5] [H]C([H])c1c([H])c(N([H])c2nc(═O) O[*:2] c2nc(═O)n(C([H])([H]) ([H])O[*:6]n(C([H])([H])[*:1])c([*:4]) [*:1])c([*:4])c2[H]) c2[H])c([H])c([H])c([H])c([H])c1C(═O) c1C(═O)OC([H])([H])[H] OC([H])([H])[H]

TABLE 1-E R1 R2 R3 R4 R5 1. [H]O[*:1].[H]Oc [H][*:2][H]Oc(c([H])c(OC([H]) [H]Oc(c [H]Oc(c([H])c (c([H]):[*:4]):[*:1]([H])[H]):[*:5])c([H])c ([H]):[*:4]):[*:1] (OC([H]) ([*:3]):[*:5].[H]([H])[H]):[*:5])c [*:3].[H][*:3] ([H])c([*:3]):[*:5] 2. [H]Oc(c [H][*:2][H]Oc(c([H])c(OC([H]) [H]Oc(c [H]Oc(c([H])c ([H]):[*:4]):[*:1].[H]([H])[H]):[*:5])c(O[H])c ([H]):[*:4]):[*:1] (OC([H]) [*:1]([*:3]):[*:5].[H] ([H])[H]):[*:5])c [*:3].[H][*:3] (O[H])c([*:3]):[*:5]3. [H]Oc(c [H][*:2] [H]Oc(c([H])c([*:3]):[*:5])c [H]Oc(c [H]Oc(c([H])c([H]):[*:4]):[*:1].[H] (O[H])c(OC([H]) ([H]):[*:4]):[*:1]([*:3]):[*:5])c(O[H])c [*:1] ([H])[H]):[*:5].[H] (OC([H])([H])[*:3].[H][*:3] [H]):[*:5] 4. [H]C([H])([H])n [H][*:2][H]C([H])([H])n1c(═O)c [H]/C(═N\[*:4])N [H][*:5].[H] 1c(═O)c(n:[*:1])(n:[*:1])c(n:[*:3])n(C (C([H])([H])[H])C [*:5].[H][*:5]c(n:[*:3])n(C([H]) ([H])([H])[H])c1═O ([H])([H])[H] ([H])[H])c1═O 5.[H]c(n:[*:2])n(c [H]c(n:[*:2])n(c [H]C([H])([H])[*:3].n[H]C([H])([H])[*:4] n(:[*:3]):[*:5].o (═O):[*:1])C([H])(═O):[*:1])C([H]) (:[*:3]):[*:5] (:[*:1]):[*:5] ([H])C(═O)N([H])([H])C(═O)N([H])[H] [H].o(:[*:1]):[*:5] 6. [H]c(n:[*:2])n(c[H]c(n:[*:2])n(c [H]C([H])([H])[*:3].n [H]C([H])([H])[*:4]n(:[*:3]):[*:5].o (═O):[*:1])C([H]) (═O):[*:1])C([H]) (:[*:3]):[*:5](:[*:1]):[*:5] ([H])[H].o(:[*:1]):[*:5] ([H])[H] 7. [H]Oc(c[H]Oc(c([H])c(OC([H]) [H]Oc(c([H])c(OC([H]) [H]Oc(c[H]Oc(c([H])c(OC([H]) ([H]):[*:4]):[*:1].[H] ([H])[H])c(OC([H])([H])([H])[H])c(OC([H]) ([H]):[*:4]):[*:1] ([H])[H])c(OC([H]) [*:1][*:2]):[*:5])c([*:3]):[*:5] ([H])[*:2]):[*:5])c ([H])[*:2]):[*:5])c([*:3]):[*:5].[H] ([*:3]):[*:5] [*:3].[H][*:3] 8. [H][O:0][c:0]([c:0][O:0]═[*:2] [H][O:0][*:3].[H] [H][O:0][c:0] [H][C:0]([H])([H])([H])[c:0]([O:0] [c:0](:[*:3]):[*:5] ([c:0]([H]) [*:5].[H][c:0][C:0]([H])([H])[H]) [c:0]([O:0][C:0] (:[*:3]):[*:5] [c:0]([Cl:0])[c:0]([H])([H]) ([o:0]:[*:4]):[*:1]):[*:1] [H])[c:0]([Cl:0]) [c:0]([o:0]:[*:4]):[*:1]):[*:1] 9. [H]Oc(c [H]Oc(c(OC([H])([H])[H])c[H]Oc(c(OC([H]) [H]Oc(c [H]Oc(c(OC([H]) ([H]):[*:4]):[*:1].[H]([H])c([*:3]):[*:5])c(C ([H])[H])c ([H]):[*:4]):[*:1] ([H])[H])c [*:1]([H])([H])O[*:2]):[*:5] ([H])c([*:3]):[*:5])c(C ([H])c([*:3]):[*:5])c([H])([H])O (C([H])([H])O[*:2]):[*:5] [*:2]):[*:5].[H] [*:3].[H][*:3]10. [H]Oc(c([H])c O═[*:2] [H]O[*:3].[H]c [H]Oc(c([H])c [H]C([H])(O[H]):[*:1])c([H])c (:[*:3]):[*:5] (O[H]):[*:1])c ([H])[*:5].[H]c(o:[*:4]):[*:1] ([H])c(o:[*:4]):[*:1] (:[*:3]):[*:5] 11. [H]Oc(c[H]Oc(c(OC([H])([H])[H])c [H]Oc(c(OC([H]) [H]Oc(c [H]Oc(c(OC([H])([H]):[*:4]):[*:1].[H] (OC([H])([H])[H])c ([H])[H])c ([H]):[*:4]):[*:1]([H])[H])c [*:1] ([*:3]):[*:5])c(C([H]) (OC([H])([H])[H])c(OC([H])([H])[H])c ([H])O[*:2]):[*:5] ([*:3]):[*:5])c([*:3]):[*:5])c(C([H]) (C([H])([H])O ([H])O[*:2]):[*:5] [*:2]):[*:5].[H][*:3].[H][*:3] 12. [H]c(c(OC([H]) O═[*:2] [H]O[*:3].[H]c [H]c(c(OC([H])[H]O[*:5].[H]c ([H])[H])c(OC([H]) (:[*:3]):[*:5] ([H])[H])c(OC(:[*:3]):[*:5] ([H])[H])c ([H])([H])[H])c (o:[*:4]):[*:1])c(o:[*:4]):[*:1])c ([H]):[*:1] ([H]):[*:1] 13. [H]Oc(c([H])c O═[*:2][H]Oc(:[*:3]):[*:5].[H] [H]Oc(c([H])c [H]C([H])([H])O(O[H]):[*:1])c([H])c [*:3] (O[H]):[*:1])c [*:5].[H]Oc (o:[*:4]):[*:1]([H])c(o:[*:4]):[*:1] (:[*:3]):[*:5] 14. [H]c1c(OC([H]) O═[*:2][H]O[*:3].[H]c [H]c1c(OC([H]) [H]O[*:5].[H]c ([H])[H])c(OC([H])(:[*:3]):[*:5] ([H])[H])c(OC (:[*:3]):[*:5] ([H])[H])c([H])c ([H])([H])([*:1])c1OC([H])([H])c [H])c([H])c (o:[*:41):[*:1]([*:1])c1OC([H])([H])c (o:[*:4]):[*:1] 15. [H]O[C@@](C([H]) O═[*:2][H]Oc(c([H])c(OC [H]O[C@@](C([H]) [H]O[*:5].[H]Oc(c([H])c([H])[H])(C([H]) ([H])([H]) ([H])[H]) (OC([H])([H])[H])c([H])[*:4])[*:1]. [H])c([H]):[*:3])c (C([H])([H])[*:4])[*:1]([H]):[*:3])c [H][*:1].[H][*:1] (:[*:3]):[*:5] (:[*:3]):[*:5] 16.[H]Oc(c [H]Oc(c([H])c [H]Oc(c([H])c [H]Oc(c [H]Oc(c([H])c([H]):[*:4]):[*:1].[H] ([*:3]):[*:5])c ([*:3]):[*:5])c([H]):[*:4]):[*:1] ([*:3]):[*:5])c [*:1] (OC([H])([H])[H])c(OC([H])([H])[H])c (OC([H])([H])[H])c ([C@@]([H]) ([C@@]([H]) ([C@@](O[H])O (O[H])O[*:2]):[*:5].[H] ([H])(O[H])O[*:2]):[*:5] [*:2]):[*:5][*:3].[H][*:3] 17. [H]C([H])([H])O [H][*:2] [H]Oc(c([H])c [H]Oc(c[H]Oc(c([H])c [*:1].[H]Oc ([*:3]):[*:5])c ([H]):[*:4]):[*:1]([*:3]):[*:5])c (c([H]):[*:4]):[*:1] (O[H])c(OC([H]) (O[H])c(OC([H])([H])[H]):[*:5]. ([H])[H]):[*:5] [H][*:3].[H][*:3] 18. [H]Oc(c([H])c(cO═[*:2] [H]C([H])([H])Oc [H]Oc(c([H])c [H]C([H])([H])O(OC([H])([H])[H])c (:[*:3]):[*:5].[H]O[*:3] (c(OC([H]) [*:5].[H]C(C(═O)[*:4]):[*:1])C ([H])[H])c(C ([H])([H])Oc ([H])([H])O[H]):[*:1](═O)[*:4]):[*:1])C (:[*:3]):[*:5] ([H])([H])O[H]):[*:1] 19.[H]Oc(c([H])c O═[*:2] [H]C([H])([H])O [H]O[*:4] [H]C([H])([H])Oc([H]):[*:1])c(OC([H]) [*:3].[H]C([H]) (:[*:3]):[*:5].[H]Oc(c([H])[H])c(n(C([H]) ([H])Oc(:[*:3]):[*:5] ([H])c([H]):[*:1])c(OC([H])[H]):[*:5]):[*:1] ([H])([H])[H])c(n(C ([H])([H]) [H]):[*:5]):[*:1]20. [H]Oc(c [H]Oc(c(OC([H]) [H]Oc(c(OC([H]) [H]Oc(c [H]Oc(c(OC([H])([H]):[*:4]):[*:1].[H] ([H])[H])c ([H])[H])c ([H]):[*:4]):[*:1]([H])[H])c [*:1] (OC([H])([H]) (OC([H])([H]) (OC([H])([H])[*:2]):[*:5])c [*:2]):[*:5])c [*:2]):[*:5])c (OC([H])([H])[H])c(OC([H])([H])[H])c (OC([H])([H])[H])c ([*:3]):[*:5] ([*:3]):[*:5].[H]([*:3]):[*:5] [*:3].[H][*:3] 21. [H]c(c(OC([H]) O═[*:2] [H]C([H])([H])Oc[H]c(c(OC([H]) [H]C([H])([H])Oc ([H])[H])c(OC([H])(:[*:3]):[*:5].[H]O[*:3] ([H])[H])c(OC (:[*:3]):[*:5].[H]O[*:5]([H])[H])c(n(C([H]) ([H])([H])[H])c ([H])[H]):[*:4]):[*:1])c (n(C([H])([H]):[*:1] ([H])[H]):[*:4]):[*:1])c ([H]):[*:1] 22.[H]Oc(c([H])c(OC([H]) O═[*:2] [H]C([H])([H])Oc [H]Oc(c([H])c[H]C([H])([H])Oc ([H])[H]):[*:1])c (:[*:3]):[*:5].[H]O[*:3] (OC([H])(:[*:3]):[*:5].[H][*:5] ([H])c(o:[*:4]):[*:1] ([H])[H]):[*:1])c ([H])c(o:[*:4]):[*:1] 23. [H]Oc(c([H])c(OC([H]) O═[*:2] [H]O[*:3].[H]c[H]C([H]) [H]C([H])([H]) ([H])[H])c([H])c (:[*:3]):[*:5] ([H])O[*:4][*:5].[H]c (O[H]):[*:1]):[*:1] (:[*:3]):[*:5] 24. [H]Oc(c(OC([H])O═[*:2] [H]C([H])([H])O [H]Oc(c(OC([H]) [H]O[*:5].[H]c ([H])[H])c(OC[*:3].[H]c ([H])[H])c (:[*:3]):[*:5] ([H])([H])[H])c (:[*:3]):[*:5](OC([H])([H])[H])c ([H])c(o:[*:4]):[*:1]):[*:1] ([H])c(o:[*:4]):[*:1]):[*:1] 25. [H]Oc(c([H])c(OC O═[*:2] [H]O[*:3].[H]c[H]Oc(c([H])c(OC([H]) [H]C([H])([H]) ([H])([H])[H])c (:[*:3]):[*:5]([H])[H])c([H])c [*:5].[H]c ([H])c(o:[*:4]):[*:1]):[*:1](o:[*:4]):[*:1]):[*:1] (:[*:3]):[*:5] 26. [H]Oc(c([H])c([H])c O═[*:2][H]C([H])([H])O [H]Oc(c([H])c([H])c [H]O[*:5].[H]c (o:[*:4]):[*:1])c[*:3].[H]c (o:[*:4]):[*:1])c(OC (:[*:3]):[*:5] (OC([H])([H])[H]):[*:1](:[*:3]):[*:5] ([H])([H])[H]):[*:1] 27. [H]Oc(c([H])c([H])c O═[*:2][H]C([H])([H])O [H]Oc(c([H])c([H])c [H]C([H])([H])Oc([H]):[*:1])c(n(C([H]) [*:3].[H]C([H])([H])Oc ([H]):[*:1])c(n(C([H])(:[*:3]):[*:5].[H]O[*:5] ([H])[H]):[*:4]):[*:1] (:[*:3]):[*:5]([H])[H]):[*:4]):[*:1] 28. [H]Oc(c([H])c O═[*:2] [H]C([H]) [H]Oc(c([H])c[H]O[*:5].[H]c (O[H]):[*:1])c([H])c(C ([H])[*:3].[H]c (O[H]):[*:1])c(:[*:3]):[*:5] (═O)[*:4]):[*:1] (:[*:3]):[*:5] ([H])c(C(═O)[*:4]):[*:1]29. [H]Oc(c([H])c([H])c O═[*:2] [H]C([H]) [H]Oc(c([H])c [H]O[*:5].[H]c([H])c(C([H])([H]) ([H])[*:3].[H]c ([H])c([H])c (:[*:3]):[*:5][*:4]):[*:1]):[*:1] (:[*:3]):[*:5] (C([H])([H]) [*:4]):[*:1]):[*:1]

Tab1e 2-A R1 R2 R3 R4 R5 1. [H]N(S(═O)(═O)N═[*:2])[H]N(S(═O)(═O)N═[*:2])[*:1]. [H]N(C(═O)C([H]) [H][*:4] [H][*:5].[H]c[*:1].[H]c(:[*:1]):[*:5] [H]N([H])[*:2] ([H])C([H])([H])[H])C(:[*:1]):[*:5] ([H])([H])C(C([H]) ([H])[H])(C([H]) ([H])[H])C([H])([H])O[*:3] 2. [H]n(c(═O)n:[*:2]):[*:1].s(: [H]N([H])[*:2].[H]n(c(═O)[H]C([H])([H])[*:3] s(:[*:1]):[*:4] [H][*:5].[H][*:5]. [*:1]):[*:4]n:[*:2]):[*:1] [H][*:5] 3. [H]c1c([H])c(OC([H])([H])[H]N([H])[*:2].[H]c1c([H]) [H][*:3] s(:[*:1]):[*:4] [H][*:5].[H][*:5].[H])c([H])c(N([H])C(═O)C( c(OC([H])([H])[H])c([H])c(N [H][*:5][H])([H])n(c(═O)n:[*:2]):[*: ([H])C(═O)C([H])([H])n(c1])c1[H].s(:[*:1]):[*:4] (═O)n:[*:2]):[*:1])c1[H] 4.[H]n(c(═S)n:[*:2]):[*:1].s(: [H]N([H])[*:2].[H]n(c(═S)n:[H]C([H])(C([H])([H]) s(:[*:1]):[*:4] [H]C([H])(C([H]) [*:1]):[*:4][*:2]):[*:1] [*:3])C([H])([H])[*:5] ([H])[*:3])C([H])([H])[*:5].[H][*:5]. [H][*:5] 5. [H]n(c(═S)n:[*:2]):[*:1].s(:[H]N([H])[*:2].[H]n(c(═S)n: [H]C([H])(C([H])([H]) s(:[*:1]):[*:4][H]C([H])(C([H]) [*:1]):[*:4] [*:2]):[*:1] [*:5])[*:3] ([H])[*:5])[*:3].[H][*:5].[H][*:5] 6. [H]c1c([H])c([H])c(N([H])C[H]N([H])[*:2].[H]c1c([H]) [H][*:3] s(:[*:1]):[*:4] [H][*:5].[H][*:5].(═O)C([H])([H])n(c(═O)n: c([H])c(N([H])C(═O)C([H]) [H][*:5][*:2]):[*:1])c([H])c1[H].s(: ([H])n(c(═O)n:[*:2]):[*:1])c [*:1]):[*:4]([H])c1[H] 7. [H]n(c(═S)n:[*:2]):[*:1].s(: [H]N([H])[*:2].[H]n(c(═S)n:[H]C([H])([H])C([H]) s(:[*:1]):[*:4] [H]C([H])([H])C [*:1]):[*:4][*:2]):[*:1] (C([H])([H])C([H]) ([H])(C([H])([H])C ([H])[*:3])[*:5]([H])([H])[*:3]) [*:5].[H][*:5].[H][*:5] 8. [H]n(c(═S)n:[*:2]):[*:1].s(:[H]N([H])[*:2].[H]n(c(═S)n: [H]c1c([H])c([H])c s(:[*:1]):[*:4][H][*:5].[H][*:5]. [*:1]):[*:4] [*:2]):[*:1] (C([H])([H])N(C([H])[H]c1c([H])c([H])c ([H])C([H])([H]) (C([H])([H])N(C [*:3])[*:5])c([H])c([H])([H])C([H]) 1[H] ([H])[*:3])[*:5])c ([H])c1[H] 9.[H]c1c([H])c(N([H])C(═O)C [H]N([H])[*:2].[H]c1c([H]) [H][*:3]s(:[*:1]):[*:4] [H][*:5].[H][*:5]. ([H])([H])n(c(═O)n:[*:2]):c(N([H])C(═O)C([H])([H])n [H][*:5] [*:1])c([H])c([H])c1OC([H])(c(═O)n:[*:2]):[*:1])c([H])c ([H])[H].s(:[*:1]):[*:4]([H])c1OC([H])([H])[H] 10. [H]n(c(═S)n:[*:2]):[*:1].s[H]N(C([H])([H])[H])[*:2]. [H]C([H])(C([H])([H]) s(:[*:1]):[*:4][H]C([H])(C([H]) (:[*:1]):[*:4] [H]n(c(═S)n:[*:2]):[*:1][*:3])C([H])([H])[*:5] ([H])[*:3])C([H]) ([H])[*:5].[H][*:5]. [H][*:5]11. [H]c1c([H])c([H])c(N([H])C [H]N([H])[*:2].[H]c1c([H]) [H][*:3]s(:[*:1]):[*:4] [H][*:5].[H][*:5]. (═O)C([H])([H])n(c(═O)n:c([H])c(N([H])C(═O)C([H]) [H][*:5] [*:2]):[*:1])c(OC([H])([H])([H])n(c(═O)n:[*:2]):[*:1])c [H])c1[H].s(:[*:1]):[*:4](OC([H])([H])[H])c1[H] 12. [H]n(c(═O)c(C#N):[*:2]):[H]N([H])[*:2].[H]n(c(═O)c [H]C([H])(C([H])([H]) s(:[*:1]):[*:4][H]C([H])(C([H]) [*:1].s(:[*:1]):[*:4] (C#N):[*:2]):[*:1] [*:5])[*:3]([H])[*:5])[*:3]. [H][*:5].[H][*:5] 13. [H][c:0]1[c:0]([H])[c:0][H][N:0]([H])[*:2].[H][c:0] [H][*:3] [s:0](:[*:1]):[*:4][H][*:5].[H][*:5]. ([C1:0])[c:0]([H])[c:0]([N:0]1[c:0]([H])[c:0]([C1:0])[c:0] [H][*:5] ([H])[C:0](═[O:0])[C:0]([H])([H])[c:0]([N:0]([H])[C:0] ([H])[n:0]([c:0](═[O:0])[n:0]:(=[O:0])[C:0]([H])([H])[n:0] [*:2]):[*:1])[c:0]1[H].[s:0]([c:0](═[O:0])[n:0]:[*:2]): (:[*:1]):[*:4] [*:1])[c:0]1[H] 14.[H]c1c([H])c([H])c(N([H])C [H]N([H])[*:2].[H]c1c([H])[H]C([H])(C([H])([H])C s(:[*:1]):[*:4] [H]C([H])(C([H])(═O)C([H])([H])n(c(═O)n: c([H])c(N([H])C(═O)C([H])([H])([H])[*:5])C([H]) ([H])C([H])([H]) [*:2]):[*:1])c(OC([H])([H])([H])n(c(═O)n:[*:2]):[*:1])c ([H])[*:3] [*:5])C([H])([H])[H])c1[H].s(:[*:1]):[*:4] (OC([H])([H])[H])c1[H] [*:3].[H][*:5].[H][*:5] 15. [H]C([H])(O[*:1])[*:4].[H]c [H][*:2].[H]c(c(OC([H])[H][*:3].[H][*:3] [H]C([H])(O[*:1]) O═[*:5].[H]Oc1nc(c(OC([H])([H])[H]):[*:1])c ([H])[H]):[*:1])c([H]):[*:2] [*:4].[H][*:4](C([H])([H])C([H]) ([H]):[*:2] ([H])N([H])[*:5]) nc(N([H])[H])c1[H] 16.[H]c1nc(C([H])([H])[H])nc O═[*:2].[H]c1nc(C([H]) [H]C([H])([H])[*:3]s(:[*:1]):[*:4] [H][*:5].[H][*:5]. (N([H])C([H])([H])C([H])([H])[H])nc(N([H])C([H])([H]) [H][*:5] ([H])c(n:[*:1])n([H]):[*:2])c1CC([H])([H])c(n:[*:1])n([H]): ([H])([H])C([H])([H])[H].[*:2])c1C([H])([H])C([H]) s(:[*:1]):[*:4] ([H])[H] 17.[H]c1c([H])c(OC([H])([H]) [H]N([H])[*:2].[H]c1c([H])[H]C([H])(C([H])([H])C s(:[*:1]):[*:4] [H]C([H])(C([H])[H])c([H])c(N([H])C(═O)C c(OC([H])([H])[H])c([H])c([H])([H])[*:5])C([H]) ([H])C([H])([H]) ([H])([H])n(c(═O)n:[*:2]):(N([H])C(═O)C([H])([H])n(c ([H])[*:3] [*:5])C([H])([H])[*:1])c1[H].s(:[*:1]):[*:4] (═O)n:[*:2]):[*:1])c1[H] [*:3].[H][*:5].[H][*:5] 18. [H][c:0]1[c:0]([H])[c:0] [H][*:2].[H][c:0](:[*:2]):[H][C:0]([H])([H]) [H][*:4] [H][*:5].[H][c:0]([Br:0])[c:0]([H])[c:0]([C:0]2= [*:5] [C:0]([H])([H])[O:0](:[*:2]):[*:5] [N:0][O:0][C:0]3([N:0]2[H]) [*:3][C:0]([H])([H])[C:0]([H])([H]) [N:0]([*:1])[C:0]([H])([H])[C:0]3([H])[H])[c:0]1[H]. [O:0]=[*:1] 19. [H]n(c(═S)n:[*:2]):[*:1].s[H]c1c([H])c([H])c(N([H]) [H]C([H])([H])N(C([H]) s(:[*:1]):[*:4][H]C([H])([H])N (:[*:1]):[*:4] [*:2])c([H])c1[H].[H]n(c ([H])C([H])([H])(C([H])([H])C([H]) (═S)n:[*:2]):[*:1] [*:3])[*:5] ([H])[*:3])[*:5].[H][*:5].[H][*:5] 20. [H][*:1].[H]c(c([H]):[*:1])c[H][*:2].[H]c(c([H]):[*:1])c [H]Oc1c([H])c(O[*:3])c [H][*:4].[H][*:4]O═[*:5].[H]Oc1c ([H]):[*:2] ([H]):[*:2] ([*:5])c(O[H])c1OC([H])c(O[*:3])c ([H])([H])[H][H][*:3] ([*:5])c(O[H])c1OC ([H])([H])[H]21. [H][*:1].[H]c(c([H]):[*:1])c [H][*:2].[H]c(c([H]):[*:1])c[H]Oc1c([H])c(O[H])c [H][*:4].[H][*:4] O═[*:5].[H]Oc1c ([H]):[*:2]([H]):[*:2] ([*:5])c(O[*:3])c1OC ([H])c(O[H])c ([H])([H])[H].[H][*:3]([*:5])c(O[*:3])c1OC ([H])([H])[H] 22. [H]O[*:1].[H]Oc(c(C(═O)C[H][*:2].[H][*:2].[H][*:2] [H]C([H])([H])O[*:3] [H]Oc(c(C(═O)[H][*:5].[H][*:5]. ([H])([H])C([H])([H])c1c([H])c C([H])([H])C([H])[H][*:5] ([H])c([H])c([H])c1[H]): ([H])c1c([H])c [*:1]):[*:4]([H])c([H])c ([H])c1[H]):[*:1]): [*:4] 23. [H]N([H])C(═O)C([H])([H])n[H]N([H])C(═O)C([H])([H])n [H]C([H])(C([H]) s(:[*:1]):[*:4][H]C([H])(C([H]) (c(═O)n:[*:2]):[*:1].s (c(═O)n:[*:2]):[*:1].[H]N([H])[*:5])[*:3] ([H])[*:5])[*:3]. (:[*:1]):[*:4] ([H])[*:2][H][*:5].[H][*:5] 24. [H]C([H])═C(C([H])([H]) [H]C([H])═C(C([H])([H])[H][*:3] s(:[*:1]):[*:4] [H][*:5].[H][*:5]. [H])C([H])([H])n(c(═O)[H])C([H])([H])n(c(═O)n: [H][*:5] n:[*:2]):[*:1].s(:[*:1]):[*:4][*:2]):[*:1].[H]N([H])[*:2] 25. [H]N([H])C(═O)C([H])([H])[H]N([H])C(═O)C([H])([H])n [H]C([H])(C([H])([H]) s(:[*:1]):[*:4][H]C([H])(C([H]) n(c(═O)n:[*:2]):[*:1].s (c(═O)n:[*:2]):[*:1].[H]N[*:3])C([H])([H])[*:5] ([H])[*:3])C([H]) (:[*:1]):[*:4] ([H])[*:2]([H])[*:5].[H][*:5]. [H][*:5] 26. [H][*:1].[H]n(:[*:1]):[*:4][H]N(C(═O)C([H])([H])[H])C [H]Oc(c(OC([H]) [H]n(:[*:1]):[*:4][H]Oc(c(OC([H]) ([H])([H])[*:2].[H][*:2]. ([H])[H])c(O[H]):([H])[H])c(O[H]): [H][*:2] [*:5]):[*:3] [*:5]):[*:3].[H][*:5] 27.[H]c1c([H])c([H])c [H]/C(═N\[*:2])N(C([H])([H]) [H]C([H])([H])[*:3]s(:[*:1]):[*:4] N#[*:5] (-c(n:[*:1])n:[*:2])c [H])C([H])([H])[H].[H]c([H])c1[H]s(:[*:1]):[*:4] 1c([H])c([H])c (-c(n:[*:1])n:[*:2])c([H])c1[H]28. [H]c(n:[*:1])n:[*:2].s [H]c(n:[*:1])n:[*:2].[H]c1c[H]C([H])([H])[*:3] s(:[*:1]):[*:4] [H][*:5].[H][*:5]. (:[*:1]):[*:4](C([H])([H])[H])nc(C([H])([H])C [H][*:5] ([H])([H])N([H])[*:2])n([H])c1═O 29. [H]C([H])([H])Oc(c(C([H]) [H][*:2].[H][*:2].[H][*:2][H]c1c([H])c([H])c [H]C([H])([H]) O═[*:5].[H]c1c([H])[H]):[*:1]):[*:4].[H]O (C([H])(O[*:3])C Oc(c(C([H])([H])([H])c([H])c(C([H]) [*:1] ([H])([H])[*:5])c [H]):[*:1]):[*:4](O[*:3])C([H]) ([H])c1[H] ([H])[*:5])c([H])c1 [H] 30.[H]n(c(═O)c(C#N):[*:2]): [H]N([H])[*:2].[H]n(c(═O)c [H]C([H])(C([H])s(:[*:1]):[*:4] [H]C([H])(C([H]) [*:1].s(:[*:1]):[*:4](C#N):[*:2]):[*:1] ([H])[*:3])C([H]) ([H])[*:3])C([H]) ([H])[*:5]([H])[*:5].[H][*:5]. [H][*:5] 31. [H]c(n:[*:1])n([H]):[*:2].sO═[*:2].[H]c(n:[*:1])n [H]C([H])([H])[*:3] s(:[*:1]):[*:4]O═[*:5].[H]c1c (:[*:1]):[*:4] ([H]):[*:2] ([H])c([H])c(N([H])[*:5])c([H])c1[H] 32. [H]c1c([H])c([H])c(N([H])C[H]N([H])[*:2].[H]c1c([H]) [H]C([H])(C([H]) s(:[*:1]):[*:4][H]C([H])(C([H]) (═O)C([H])([H])n(c(═O)n: c([H])c(N([H])C(═O)C([H])([H])[*:5])[*:3] ([H])[*:5])[*:3]. [*:2]):[*:1])c([H])c1[H].s([H])n(c(═O)n:[*:2]):[*:1])c [H][*:5].[H][*:5] (:[*:1]):[*:4] ([H])c1[H]33. [H]n(c(═S)n:[*:2]):[*:1].s [H]N([H])[*:2].[H]n(c(═S)n:[H]C([H])([H])C(S s(:[*:1]):[*:4] [H]C([H])([H])C (:[*:1]):[*:4][*:2]):[*:1] [*:5])(C([H])([H]) (S[*:5])(C([H]) [H])C([H])([H])[*:3]([H])[H])C([H])([H]) [*:3].[H][*:5].[H][*:5] 34.[H]c1c([H])c(N([H])C(═O)C [H]N([H])[*:2].[H]c1c([H]) [H]C([H])(C([H])s(:[*:1]):[*:4] [H]C([H])(C([H]) ([H])([H])n(c(═O)n:[*:2]):c(N([H])C(═O)C([H])([H])n ([H])[*:5])[*:3] ([H])[*:5])[*:3].[*:1])c([H])c([H])c1OC([H]) (c(═O)n:[*:2]):[*:1])c([H])c[H][*:5].[H][*:5] ([H])[H].s(:[*:1]):[*:4] ([H])c1OC([H])([H])[H] 35.[H]c1c([H])c(N([H])C(═O)C [H]N([H])[*:2].[H]c1c([H]) [H]C([H])(C([H])s(:[*:1]):[*:4] [H]C([H])(C([H]) ([H])([H])n(c(═O)n:[*:2]):c(N([H])C(═O)C([H])([H])n ([H])C([H])([H]) ([H])C([H])([H])[*:1])c([H])c([H])c1OC([H]) (c(═O)n:[*:2]):[*:1])c([H])c[*:5])C([H])([H])[*:3] [*:5])C([H])([H]) ([H])[H].s(:[*:1]):[*:4]([H])c1OC([H])([H])[H] [*:3].[H][*:5].[H] [*:5] 36.[H]n(c(═S)n:[*:2]):[*:1].s [H]c1c([H])c([H])c(C([H])([H]C([H])([H])C([H]) s(:[*:1]):[*:4] [H]C([H])([H])C (:[*:1]):[*:4][H])N([H])[*:2])c([H])c1[H]. (C([H])([H])C([H]) ([H])(C([H])([H])C[H]n(c(═S)n:[*:2]):[*:1] ([H])[*:3])[*:5] ([H])([H])[*:3])[*:5].[H][*:5].[H] [*:5] 37. [H]c1c([H])c([H])c(N([H])C[H]N([H])[*:2].[H]c1c([H]) [H]C([H])([H])C s(:[*:1]):[*:4][H][*:5].[H][*:5]. (═O)C([H])([H])n(c(═O)n: c([H])c(N([H])C(═O)C([H])([H])([H])[*:3] [H][*:5] [*:2]):[*:1])c(OC([H])([H])([H])n(c(═O)n:[*:2]):[*:1])c [H])c1[H].s(:[*:1]):[*:4](OC([H])([H])[H])c1[H] 38. [H]c(n:[*:1])n:[*:2].s(:[*:1]):[H]N(C([H])([H])C([H])([H])C [H]C([H])([H])[*:3] s(:[*:1]):[*:4][H][*:5].[H][*:5]. [*:4] ([H])([H])c1nc(═O)n([H])n1 [H][*:5][H])[*:2].[H]c(n:[*:1])n: [*:2] 39. [H]c1c([H])c([H])c(N([H])C[H]N([H])[*:2].[H]c1c([H]) [H]C([H])(C([H]) s(:[*:1]):[*:4][H]C([H])(C([H]) (═O)C([H])([H])n(c(═O)n:[*: c([H])c(N([H])C(═O)C([H])([H])[*:5])[*:3] ([H])[*:5])[*:3]. 2]):[*:1])c(OC([H])([H])[H])c1([H])n(c(═O)n:[*:2]):[*:1])c [H][*:5].[H][*:5] [H].s(:[*:1]):[*:4](OC([H])([H])[H])c1[H]

Tab1e 2-B R1 R2 R3 R4 R5 1. [H]Oc1c([H])c2c(c [H]O[*:2] [H]O[*:3][H][*:4] [H]Oc1c([H])c2c(c([H])c ([H])c1OC([H])([H])1OC([H])([H])[H])C([H]) [H])C([H])([H])C2(C ([H])C2(C(═O)[*:1])C(═O)[*:1])C([H])([H]) ([H])([H])O[*:5] O[*:5] 2. [H]Oc1c([H])c(C[H]O[*:2] [H]O[*:3] [H][*:4] [H]Oc1c([H])c(C([H])([H])([H])([H])C([H])(C(═O) C([H])(C(═O)[*:1])C([H]) [*:1])C([H])([H])O([H])O[*:5])c([H])c([H]) [*:5])c([H])c([H])c1O c1OC([H])([H])[H]C([H])([H])[H] 3. [H][*:1] [H]O[*:2] [H]O[*:3] [H][*:4][H]Oc1c([H])c(OC([H])([H]) [H])c([H])c2c1C(═O) C([H])([H])C([H])([*:5])O2 4. [H]Oc1c([H])c([C@@] [H]O[*:2] [H]O[*:3] [H][*:4][H]Oc1c([H])c([C@@]([H]) ([H])(O[*:5])C([H]) (O[*:5])C([H])([H])C([H])C(═O)[*:1])c (═O)[*:1])c([H])c([H])c1 ([H])c([H])c1OC([H])OC([H])([H])[H] ([H])[H] 5. [H]Oc1c([H])c(C([H]) [H]O[*:2] [H]O[*:3][H][*:4] [H]Oc1c([H])c(C([H]) (O[*:5])C([H])([H])C(O[*:5])C([H])([H])C(═O) (═O)[*:1])c([H])c [*:1])c([H])c([H])c1OC([H])([H])c1OC([H])([H])[H] ([H])[H] 6. [H]Oc1c([H])c([C@@] [H]O[*:2][H]O[*:3] [H][*:4] [H]Oc1c([H])c([C@@] ([H])(O[*:5])C([H])([H])(O[*:5])C([H])([H])C ([H])C(═O)[*:1])c (═O)[*:1])c([H])c([H])c1([H])c([H])c1OC([H]) OC([H])([H])[H] ([H])[H] 7. [H]Oc1c([H])c(C([H])[H]O[*:2] [H]O[*:3] [H][*:4] [H]Oc1c([H])c(C([H]) (O[*:5])C([H])(O[H])C(O[*:5])C([H])(O[H])C([H]) ([H])([H])[*:1]) ([H])[*:1])c([H])c([H])c1c([H])c([H])c1OC([H]) OC([H])([H])[H] ([H])[H] 8. [H]Oc1c([H])c([C@@][H]O[*:2] [H]O[*:3] [H][*:4] [H]Oc1c([H])c([C@@] ([H])(O[*:5])C([H])([H])(O[*:5])C([H])([H])C ([H])C([H])([H])[*:1])c([H])([H])[*:1])c([H])c([H]) ([H])c([H])c1OC c1OC([H])([H])[H]([H])([H])[H] 9. [H]Oc1c([H])c([H])c [H]O[*:2] [H]O[*:3] [H][*:4][H]Oc1c([H])c([H])c(C (C([H])(O[*:5])C([H]) ([H])(O[*:5])C([H])(O[H])(O[H])C([H])([H])[*:1])c C([H])([H])[*:1])c([H])c1([H])c1OC([H])([H])[H] OC([H])([H])[H] 10. [H]Oc1c([H])c([C@@] [H]O[*:2][H]O[*:3] [H][*:4] [H]Oc1c([H])c([C@@]([H]) ([H])(O[*:5])[C@]([H])(O[*:5])[C@]([H])(O[H]) (O[H])C([H])([H])[*:1])c C([H])([H])[*:1])c([H])([H])c([H]) c([H])c1OC([H])([H])[H] c1OC([H])([H])[H] 11.[H]Oc1c([H])c([H])c [H]O[*:2] [H]O[*:3] [H][*:4] [H]Oc1c([H])c([H])c([C([C@@]([H])(O[*:5]) @@]([H])(O[*:5])[C@]([H]) [C@]([H])(O[H])C([H])(O[H])C([H])([H])[*:1]) ([H])[*:1])c([H]) c([H])c1OC([H])([H])[H]c1OC([H])([H])[H] 12. [H][*:1] [H]O[*:2] [H]Oc1c([H])c([H])c[H]Oc1c([H])c([H])c [H]O[*:5] ([C@@]([H])(O[*:3]) ([C@@]([H])(O[*:3])[C@@]([H])(O[H])C([H]) [C@@]([H])(O[H])C ([H])[*:4])c([H])c([H])([H])[*:4])c([H])c 1OC([H])([H])[H] 1OC([H])([H])[H] 13. [H][*:1][H]O[*:2] [H]Oc1c(OC([H])([H]) [H]Oc1c(OC([H])([H]) [H][*:5][H])c([H])c([H])c2c1 [H])c([H])c([H])c2c1 OC([H])([H])C([H])OC([H])([H])C([H]) ([*:4])O2([H])O[*:3] ([*:4])O2([H])O[*:3] 14.[H]C([H])([H])O[*:1] [H]O[*:2] [H]c1c2c(c([H])c3c1 [H]c1c2c(c([H])c3c1[H]O[*:5] OC([H])([*:4])C3([H])C OC([H])([*:4])C3([H])C([H])([H])O[*:3])O ([H])([H])O[*:3])O C([H])([H])O2 C([H])([H])O2 15.[H]Oc1c([H])c([H])c [H]O[*:2] [H]C([H])([H])O[*:3] [H][*:4][H]Oc1c([H])c([H])c(C([H]) (C([H])(C(═O)[*:1]) (C(═O)[*:1])C([H])([H])C([H])([H])O[*:5])c O[*:5])c(OC([H])([H]) (OC([H])([H])[H])c1[H][H])c1[H] 16. [H][*:1] [H]O[*:2] [H]Oc1c([H])c(C([H])[H]Oc1c([H])c(C([H]) [H]O[*:5] (O[*:3])C([H])([H])C (O[*:3])C([H])([H])C(═O)[*:4])c([H])c (═O)[*:4])c([H])c ([H])c1OC([H])([H])[H]([H])c1OC([H])([H])[H] 17. [H][*:1] [H]O[*:2] [H]c1c2c(c([H])c(C([H])[H]c1c2c(c([H])c(C([H]) [H]O[*:5] (C(═O)[*:4])C([H]) (C(═O)[*:4])C([H])([H])O[*:3])c1OC([ ([H])O[*:3])c1OC H])([H])[H])OC([H])([H])([H])[H])OC([H]) ([H])O2 ([H])O2 18. [H][*:1] [H]O[*:2][H]c1c([H])c(C([H]) [H]c1c([H])c(C([H]) [H]O[*:5] (O[*:3])C([H])([H])C(O[*:3])C([H])([H])C (═O)[*:4])c([H])c([H]) (═O)[*:4])c([H])c([H])c1OC([H])([H])[H] c1OC([H])([H])[H] 19. [H][*:1] [H]O[*:2][H]Oc1c([H])c([H])c [H]Oc1c([H])c([H])c [H]C([H])([H])O[*:5](C([H])(C(═O)[*:4])C (C([H])(C(═O)[*:4])C ([H])([H])O[*:3])c(OC([H])([H])O[*:3])c(OC ([H])([H])[H])c1[H] ([H])([H])[H])c1[H] 20.[H][*:1] [H]O[*:2] [H]Oc1c([H])c(OC([H]) [H]Oc1c([H])c(OC [H]O[*:5]([H])[H])c([H])c ([H])([H])[H])c([H])c ([H])c1C ([H])c1C([H])(C(═O)([H])(C(═O)[*:4])C [*:4])C([H])([H])O[*:3] ([H])([H])O[*:3] 21.[H]Oc1c([H])c([C@@] [H]O[*:2] [H][*:3] [H][*:4] [H]Oc1c([H])c([C@@]([H])([H])(O[*:5])C([H]) (O[*:5])C([H])([H])C([H]) ([H])C([H])([H])[*:1])c([H])[*:1])c([H])c([H]) ([H])c([H])c1OC c1OC([H])([H])[H] ([H])([H])[H]22. [H][*:1] [H]O[*:2] [H]Oc1c(OC([H])([H]) [H]Oc1c(OC([H])([H])[H][*:5] [H])c(OC([H])([H])[H])c [H])c(OC([H])([H]) ([H])c([H])c1C([H])[H])c([H])c([H])c1C (C([H])([H])O[*:3])C ([H])(C([H])([H])O([H])([H])[*:4] [*:3])C([H])([H])[*:4] 23. [H][*:1] [H]O[*:2][H]Oc1c(OC([H])([H]) [H]Oc1c(OC([H])([H]) [H][*:5][H])c([H])c([H])c(C([H]) [H])c([H])c([H])c(C (C([H])([H])O[*:3])C([H])(C([H])([H])O ([H])([H])[*:4])c [*:3])C([H])([H])[*:4])c1OC([H])([H])[H] 1OC([H])([H])[H] 24. [H][*:1] [H]O[*:2] [H][*:3][H]Oc1c(OC([H])([H]) [H][*:5] [H])c(OC([H])([H]) [H])c(O[H])c2c1OC([H])([H])C([H])(C([H]) ([H])[*:4])C2═O 25. [H][*:1] [H]O[*:2][H]Oc1c([H])c(C([H]) [H]Oc1c([H])c(C([H]) [H][*:5] (O[*:3])C([H])([H])C(O[*:3])C([H])([H])C ([H])([H])[*:4])c([H]) ([H])([H])[*:4])c([H])c([H])c1OC([H])([H]) c([H])c1OC([H])([H]) [H] [H] 26. [H][*:1] [H]O[*:2][H]Oc1c(OC([H])([H]) [H]Oc1c(OC([H])([H]) [H][*:5] [H])c([H])c([H])c(C[H])c([H])c([H])c(C([H]) ([H])(C([H])([H])O (C([H])([H])O[*:3])C[*:3])C([H])([H])[*:4])c ([H])([H])[*:4])c 1OC([H])([H])[H]1OC([H])([H])[H] 27. [H][*:1] [H]O[*:2] [H]Oc1c([H])c(C([H])[H]Oc1c([H])c(C([H]) [H][*:5] ([H])C(O[H])(O[*:3]) ([H])C(O[H])(O[*:3])C(═O)[*:4])c([H])c C(═O)[*:4])c([H])c ([H])c1OC([H])([H])([H])c1OC([H])([H])[H] [H] 28. [H][*:1] [H]O[*:2] [H]Oc1c([H])c([C@[H]Oc1c([H])c([C@ [H][*:5] @]([H])(O[*:3])C([H]) @]([H])(O[*:3])C([H])([H])C([H])([H])[*:4])c ([H])C([H])([H])[*:4])c ([H])c([H])c1OC([H])([H])c([H])c1OC([H]) ([H])[H] ([H])[H] 29. [H]C([H])([H])O[*:1][H]O[*:2] [H]Oc1c([H])c(O[H]) [H][*:4] [H][*:5] c(C(═O)C([H])([H])C([H])([H])[*:3])c (O[H])c1[H] 30. [H]Oc1c([H])c([H])c [H]O[*:2][H]O[*:3] [H][*:4] [H]Oc1c([H])c([H])c(C([H]) (C([H])(O[*:5])C([H])(O[*:5])C([H])(O[H]) (O[H])C(═O)[*:1]) C(═O)[*:1])c([H])c1OCc([H])c1OC([H])([H])[H] ([H])([H])[H] 31. [H]C([H])([H])O[*:1] [H]O[*:2][H]Oc1c([H])c([H])c2 [H]Oc1c([H])c([H])c2 [H][*:5] c(c1[H])OC([H])([H])c(c1[H])OC([H])([H]) C([H])([*:3])C2([H]) C([H])([*:3])C2([H]) O[*:4]O[*:4] 32. [H]C([H])([H])O[*:1] [H]O[*:2] [H]Oc1c([H])c([H])c2[H]Oc1c([H])c([H])c2 [H][*:5] c(c1[H])OC([H])([H]) c(c1[H])OC([H])([H])C([H])([*:3])C2([H]) C([H])([*:3])C2([H]) O[*:4] O[*:4] 33.[H]C([H])([H])O[*:1] [H]O[*:2] [H][*:3] [H]Oc1c(OC([H])([H])[H]Oc1c(OC([H])([H])[H]) [H])c([H])c([H])c2c1 c([H])c([H])c2c1OC([H])OC([H])([H])C([H]) ([H])C([H])([*:4])C2([H]) ([*:4])O2([H])O[*:5] O[*:5]34. [H]c1c([H])c(C([H]) [H]O[*:2] [H]O[*:3] [H][*:4][H]c1c([H])c(C([H])(C(═O) (C(═O)[*:1])C([H]) [*:1])C([H])([H])O[*:5])c([H])O[*:5])c(OC([H]) (OC([H])([H])[H])c([H]) ([H])[H])c([H])c1OCc1OC([H])([H])[H] ([H])([H])[H] 35. [H]Oc1c([H])c([H])c [H]O[*:2][H]O[*:3] [H][*:4] [H]Oc1c([H])c([H])c(C([H]) (C([H])(O[*:5])C([H])(O[*:5])C([H])([H])C([H]) ([H])C([H])(O[H])[*:1])c(O[H])[*:1])c([H])c1[H] ([H])c1[H] 36. [H]Oc1c([H])c(OC([H]) [H]O[*:2][H]C([H])([H])O[*:3] [H][*:4] [H]Oc1c([H])c(OC([H])([H])([H])[H])c([H])c([H])c1C [H])c([H])c([H])c1C([H]) ([H])(O[*:5])C(O[*:5])C([H])([H])C ([H])([H])C(═O)[*:1] (═O)[*:1] 37.[H]Oc1c([H])c([H])c [H]O[*:2] [H]C([H])([H])O[*:3] [H]C([H])([H])O[*:4][H]Oc1c([H])c([H])c(C([H]) (C([H])([H])C([H]) ([H])C([H])(C(═O)[*:1])(C(═O)[*:1])C([H]) C([H])([H])O[*:5])c ([H])O[*:5])c([H])c1[] ([H])c1[H]38. [H]C([H])([H])O[*:1 [H]O[*:2] [H]Oc1c([H])c(OC([H])[H]Oc1c([H])c(OC([H]) [H][*:5] ] ([H])[H])c([H])c([H])c1C([H])[H])c([H])c ([H])(C([H])([H])O ([H])c1C([H])(C([H])[*:3])C([H])([H]) ([H])O[*:3])C([H]) [*:4] ([H])[*:4] 39.[H]Oc1c([H])c(C([H]) [H]O[*:2] [H]C([H])([H])O[*:3] [H][*:4][H]Oc1c([H])c(C([H])(O[*:5]) (O[*:5])C([H])([H])CC([H])([H])C(═O)[*:1])c (═O)[*:1])c([H])c ([H])c([H])c1OC([H])([H])c1OC([H])([H])[H] ([H])[H] 40. [H][*:1] [H]O[*:2][H]Oc1c([H])c([H])c [H]Oc1c([H])c([H])c [H]O[*:5] (C([H])(C(═O)[*:4])C(C([H])(C(═O)[*:4])C ([H])([H])O[*:3])c(OC ([H])([H])O[*:3])c(OC([H])([H])[H])c1[H] ([H])([H])[H])c1[H] 41. [H]Oc1c([H])c([H])c[H]O[*:2] [H]C([H])([H])O[*:3] [H]0[*:4] [H]Oc1c([H])c([H])c(C([H])(C([H])([H])C([H]) ([H])C([H])(C(═O)[*:1])C (C(═O)[*:1])C([H])([H])([H])O[*:5])c ([H])O[*:5])c([H])c1[H] ([H])c1[H] 42.[H]C([H])([H])O[*:1] [H]O[*:2] [H]Oc1c([H])c([H])c2 [H]Oc1c([H])c([H])c2[H][*:5] c(c1O[H])OC([H])([H]) c(c1O[H])OC([H])([H]) [C@](O[H])(C([H])[C@](O[H])(C([H]) ([H])[*:3])[C@]2(C ([H])[*:3])[C@]2(C([H])([H])([H])[H])[*:4] ([H])[H])[*:4] 43. 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[H]Oc1c([H])c(C(C(═O) [H]Oc1c([H])c(C [H]O[*:3][H][*:4] [H]O[*:5] [*:1])(C([H])([H])OC (C(═O)[*:1])(C([H])(═O)C([H])([H]) ([H])OC(═O)C([H]) [H])C([H])([H])O ([H])[H])C([H])([H])O[*:2])c([H])c([H])c1OC [*:2])c([H])c([H])c1OC ([H])([H])[H]([H])([H])[H] 53. [H]Oc1c([H])c(OC([H]) [H]Oc1c([H])c(OC [H][*:3][H]O[*:4] [H][*:5] ([H])[H])c([H])c([H])c1C ([H])([H])[H])c([H])c([H])(C([H]) ([H])c1C([H])(C ([H])O[*:1])C([H]) ([H])([H])O[*:1])C([H])[*:2] ([H])([H])[*:2] 54. [H]Oc1c([H])c(O[*:1]) [H]C([H])([H])[*:2][H]C([H])([H])O[*:3] [H][*:4] [H]O[*:5] c([H])c(C([H])([H]) [H])c1[H]55. [H]Oc1c([H])c([H])c [H]Oc1c([H])c([H])c [H]O[*:3] [H][*:4] [H]O[*:5](C([H])(O[*:2])C([H]) (C([H])(O[*:2])C ([H])C(═O)[*:1])c([H])([H])C(═O)[*:1]) ([H])c1OC c([H])c1OC([H])([H])[H] ([H])([H])[H]56. 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[H]Oc1c([H])c(C([H])[H]C([H])([H])O[*:2] [H]O[*:3] [H][*:4] [H]Oc1c([H])c(C([H])([H])([H])C([H])(C(═O) C([H])(C(═O)[*:1])C([H]) [*:1])C([H])([H])O([H])O[*:5])c([H])c([H]) [*:5])c([H])c([H])c1O c1OC([H])([H])[H]C([H])([H])[H] 62. [H][*:1] [H]O[*:2] [H]Oc1c([H])c([H])c2[H]Oc1c([H])c([H])c2 [H][*:5] c(c1[H])OC([H])([H]) c(c1[H])OC([H])([H])C(O[H])([*:4])C2 C(O[H])([*:4])C2 ([H])O[*:3] ([H])O[*:3] 63.[H]Oc1c([H])c2c [H][*:2] [H]O[*:3] [H][*:4] [H]Oc1c([H])c2c(c([H])c(c([H])c1C([H])(C([H]) 1C([H])(C([H])([H])O[*: ([H])O[*:5])C([H])5])C([H])(O[H])[*:1])OC (O[H])[*:1])OC([H]) ([H])([H])O2 ([H])O2 64.[H]C([H])([H])O[*:1] [H][*:2] [H]Oc1c([H])c([H])c2 [H]Oc1c([H])c([H])c2[H][*:5] c(c1[H])OC([H])([H]) c(c1[H])OC([H])([H]) C(O[H])([*:3])C2C(O[H])([*:3])C2 ([H])O[*:4] ([H])O[*:4] 65. [H]Oc1c([H])c(C([H])[H]Oc1c([H])c(C([H]) [H]O[*:3] [H][*:4] [H]O[*:5] (O[*:2])C([H])(O[H])C(O[*:2])C([H])(O[H])C (═O)[*:1])c([H])c (═O)[*:1])c([H])c1OC([H])([H])[H] ([H])c([H])c1OC([H]) ([H])[H] 66. [H][*:1][H]O[*:2] [H]Oc1c([H])c([H])c [H]Oc1c([H])c([H])c [H]O[*:5](C([H])(O[*:3])C([H]) (C([H])(O[*:3])C([H]) ([H])C(═O)[*:4])c([H])C(═O)[*:4])c ([H])c1[H] ([H])c1[H] 67. [H]Oc1c([H])c([H])c[H]O[*:2] [H]C([H])([H])O[*:3] [H][*:4] [H]Oc1c([H])c([H])c([C([C@@]([H])(O[*:5])C @@]([H])(O[*:5])C([H]) ([H])([H])C(═O)[*:1])c([H])C(═O)[*:1])c([H])c1 ([H])c1[H] [H] 68. [H]Oc1c([H])c2c(c([H])c1C[H]O[*:2] [H]O[*:3] [H][*:4] [H]Oc1c([H])c2c(c([H])c ([H])(O[*:5])C([H])1C([H])(O[*:5])C([H]) ([H])C(═O)[*:1])C1 ([H])C(═O)[*:1])C1([H])C([H])C3([H])C([H]) 3([H])C([H])(C([H])([H]) (C([H])([H])C([H])C([H])([H])C3(C([H])([H]) ([H])C3(C([H])([H]) [H])O2)C1(C([H])([H])[H])O2)C1(C([H]) [H])C([H])([H])[H] ([H])[H])C([H]) ([H])[H] 69.[H]C([H])([H])O[*:1] [H][*:2] [H]Oc1c([H])c([H])c2 [H]Oc1c([H])c([H])c2[H][*:5] c(c1O[H])OC([H]) c(c1O[H])OC([H])([H])C ([H])C([H])([*:3])C2([H])([*:3])C2([H])O[*:4] ([H])O[*:4] 70. 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[H]Oc1c([H])c(C([H]) [H]O[*:2][H]O[*:3] [H][*:4] [H]Oc1c([H])c(C([H]) (O[*:5])C([H])(O[H])C(O[*:5])C([H])(O[H])C(═O) (═O)[*:1])c([H])c [*:1])c([H])c(OC([H])([H])(OC([H])([H])[H]) [H])c1O[H] c1O[H] 75. [H]Oc1c([H])c([H])c[H]Oc1c([H])c([H])c [H]O[*:3] [H][*:4] [H]O[*:5] ([C@]([H])(O[*:2])([C@]([H])(O[*:2]) [C@@]([H])(O[H])C [C@@]([H])(O[H])C ([H])([H])[*:1])c([H])([H])[*:1])c ([H])c1O[H] ([H])c1O[H] 76. [H][*:1] [H]O[*:2][H]Oc1c([H])c([C@ [H]Oc1c([H])c([C@ [H]O[*:5] @]([H])(O[*:3])[C@@]([H])(O[*:3])[C@ @]([H])(O[H])C(═O) @]([H])(O[H])C(═O)[*:4])c([H])c([H])c1O [*:4])c([H])c([H])c1O C([H])([H])[H]C([H])([H])[H] 77. [H]Oc1c([H])c([C@ [H][*:2] [H]O[*:3] [H][*:4][H]Oc1c([H])c([C@@] @]([H])(O[*:5])C([H]) ([H])(O[*:5])C([H])([H])C([H])C(═O)[*:1])c([H])c (═O)[*:1])c([H])c([H])c1 ([H])c1OC([H])OC([H])([H])[H] ([H])[H] 78. [H][*:1] [H]O[*:2] [H]Oc1c([H])c([H])c[H]Oc1c([H])c([H])c [H]O[*:5] ([H])c([H])c1C([H])(O([H])c([H])c1C([H])(O [*:3])C([H])([H])C [*:3])C([H])([H])C (═O)[*:4](═O)[*:4] 79. 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[H]Oc1c([H])c([H])c [H][*:2][H]C(═C([H])[*:4])C [H]C(═C([H])[*:4])C [H]O[*:5] 2c(c1[H])OC([H])(O[*:3])(C([H])([H]) (O[*:3])(C([H])([H]) ([H])C([H])([*:1])C2[H])C([H])([H])[H] [H])C([H])([H])[H] ([H])[H] 84. [H]Oc1c([H])c([H])c[H]Oc1c([H])c([H])c [H]O[*:3] [H][*:4] [H]O[*:5] (C([H])(O[*:2])C([H])(C([H])(O[*:2])C ([H])C([H])(O[H]) ([H])([H])C([H])(O [*:1])c([H])c1O[H][H])[*:1])c([H])c1 O[H] 85. [H][*:1] [H]O[*:2] [H]OC([H])(C(═O)[*:4])C[H]OC([H])(C(═O)[*:4])C [H]O[*:5] ([H])(O[*:3])c1c([H])(O[*:3])c1c([H])c ([H])c([H])c(OC([H]) ([H])c(OC([H])([H])[H])c([H])[H])c([H])c1[H] ([H])c1[H] 86. [H]Oc1c([H])c([H])c[H]C([H])([H])O[*:2] [H]O[*:3] [H]C(═O)[*:4] [H]Oc1c([H])c([H])c(C(C([H])(C([H])([H]) ([H])(C([H])([H])O[*:5])C O[*:5])C([H])([H])([H])([H])[*:1])c(O[H])c1 [*:1])c(O[H])c1C([H]) C([H])([H])C([H])═C(C([H])C([H])═C(C([H]) ([H])([H])[H])C([H])([H]) ([H])[H])C([H])([H]) [H][H] 87. 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[H]Oc1c([H])c([H])c [H]O[*:2] [H]O[*:3] [H][*:4][H]Oc1c([H])c([H])c(C (C([H])(O[*:5])C([H]) ([H])(O[*:5])C([H])([H])C([H])C(═O)[*:1])c([H]) (═O)[*:1])c([H])c1O[H] c1O[H] 101. [H][*:1][Cl:0][*:2] [Cl:0][*:3] [H][c:0]1[c:0]([C:0] [H][*:5]([H])([H])[H])[s:0][c:0] 2[c:0]1[c:0]([N:0]([H]) [H])[n:0][c:0](=[O:0])[n:0]2[C:0]([H])([H]) [*:4] 102. [H][*:1] [H]O[*:2] [H]Oc1c([H])c([H])c[H]Oc1c([H])c([H])c [H]O[*:5] (C([H])([H])C([H])(C (C([H])([H])C([H])(C(═O)[*:4])C([H])([H]) (═O)[*:4])C([H])([H]) O[*:3])c([H])c1[H]O[*:3])c([H])c1[H] 103. [H]C([H])([H])O[*:1] [H][*:2][H]Oc1c([H])c([H])c [H]Oc1c([H])c([H])c [H]C([H])([H])O[*:5](C([H])(O[*:4])C([H]) (C([H])(O[*:4])C([H]) ([H])C(═O)[*:3])c([H])C(═O)[*:3])c ([H])c1[H] ([H])c1[H] 104. [H]Oc1c([H])c([H])c[H]O[*:2] [H]O[*:3] [H][*:4] [H]Oc1c([H])c([H])c(C (C([H])(C(═O)[*:1])C([H])(C(═O)[*:1])C([H]) ([H])([H])O[*:5])c ([H])O[*:5])c(O[H])c1[H](O[H])c1[H] 105. [H]C([H])([H])O[*:1] [H]C([H])([H])O[*:2][H]OC(═O)c1sc2nc [H][*:4] [H]C([H])([H])O[*:5] ([H])nc(N([H])[*:3])c2c1C([H])([H])[H] 106. [H]c1c([H])c(C([H]) [H]O[*:2] [H]O[*:3][H]C([H])([H])[*:4] [H]c1c([H])c(C([H])(C (C(═O)[*:1])C([H])(═O)[*:1])C([H]) ([H])O[*:5])c([H])c ([H])O[*:5])c([H])c1OC([H])([H])[H] ([H])c([H])c1OC([H]) ([H])[H] 107.[H]Oc1c([H])c2c(c([H]) [H]Oc1c([H])c2c(c [H]C([H])([H])O[*:3] [H]O[*:4][H][*:5] c1O[H])[N+](C([H]) ([H])c1O[H])[N+] ([H])[H])(C([H])([H])C(C([H])([H])[H])(C ([H])([H])[*:2])C ([H])([H])C([H])([H])([H])([*:1])C2([H])[H] [*:2])C([H])([*:1]) O2([H])[H] 108. [H][*:1][H]O[*:2] [H]Oc1c([H])c([H])c [H]Oc1c([H])c([H])c [H][*:5](C([H])(C([H])([H])O (C([H])(C([H])([H])O [*:3])C([H])([H])[*:4])[*:3])C([H])([H])[*:4]) c(O[H])c1[H] c(O[H])c1[H] 109. 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[H][*:1] [H]N(c1nc(C([H])[H]O[*:3] [H]C([H])([H])O[*:4] [H][*:5] ([H])[H])nc2sc3c(c12)C([H])([H])C ([H])([H])C3([H]) [H])[*:2] 114. [H]Oc1c([H])c([H])c[H]O[*:2] [H]C([H])([H])O[*:3] [H][*:4] [H]Oc1c([H])c([H])c([C([C@@]([H])(O[*:5]) @@]([H])(O[*:5]) [C@]([H])(O[H])C(═O) [C@]([H])[*:1])c([H])c1[H] (O[H])C(═O)[*:1])c ([H])c1[H] 115. [H][*:1] [H][*:2][H]OC(═NC([H])(c1c [H]OC(═NC([H])(c1c [H]O[*:5] ([H])c([H])c(OC([H])([H])c([H])c(OC([H]) ([H])[H])c(O[H])c1[H])C ([H])[H])c(O[H])c1[H])C([H])([H])[*:3])[*:4] ([H])([H])[*:3])[*:4] 116. [H]Oc1c([H])c([H])c[H]Oc1c([H])c([H])c [H]C([H])([H])O[*:3] [H][*:4] [H]O[*:5](C([H])(O[*:2])C([H]) (C([H])(O[*:2])C ([H])C(═O)[*:1])c([H])([H])([H])C(═O) c1[H] [*:1])c([H])c1[H] 117. [H]O[*:1] [H][*:2][H]Oc1c([H])c(OC([H]) [H]Oc1c([H])c(OC [H][*:5] ([H])[H])c([H])c([H])c1C([H])([H])[H])c([H])c (O[H])(C(═O)[*:3])C([H]) ([H])c1C(O[H])(C(═O)([H])O[*:4] [*:3])C([H])([H])O[*:4] 118. 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[H]Oc1c([H])c([H])c [H]Oc1c([H])c([H])c[H]O[*:3] [H][*:4] [H]O[*:5] (C([H])(O[*:2])C([H]) (C([H])(O[*:2])C(O[H])C([H])(O[H]) ([H])(O[H])C([H]) [*:1])c([H])c1O[H](O[H])[*:1])c([H])c 1O[H] 123. [H][*:1] [H]Oc1c([H])c([H])c [H]O[*:3][H]C([H])([H])O[*:4] [H][*:5] (C([H])([H])C([H]) ([H])[*:2])c([H])c1OC([H])([H])[H] 124. [H]Oc1c([H])c([C@] [H]O[*:2] [H][*:3] [H][*:4][H]Oc1c([H])c([C@]([H]) ([H])(OC([H])([H]) (OC([H])([H])[*:1])C([H])[*:1])C([H])([H])[*:5])c ([H])[*:5])c([H])c([H])c ([H])c([H])c1OC([H])1OC([H])([H])[H] ([H])[H] 125. [H]Oc1c(C([H])([H]) [H]C([H])([H])O[*:2][H]O[*:3] [H]C(═O)[*:4] [H]Oc1c(C([H])([H])C C([H])═C(C([H])([H])([H])═C(C([H])([H])[H])C [H])C([H])([H])[H])c ([H])([H])[H])c(OC([H])(OC([H])([H])[H]) ([H])[H])c([H])c([H])c1C c([H])c([H])c1C([H])([H])(C([H])([H])O[*:5])C (C([H])([H])O[*:5]) ([H])([H])[*:1]C([H])([H])[*:1] 126. [H][*:1] [H]OC([H])([H])/C [H]Oc1c([H])c([H])c[H]Oc1c([H])c([H])c [H]C([H])([H])O[*:5] ([H])═C(/[H])[*:2](C([H])(O[*:4])C([H]) (C([H])(O[*:4])C([H]) (C([H])([H])O[H])[*:3])c(C([H])([H])O[H]) ([H])c1OC([H])([H])[H] [*:3])c([H])c1OC([H]) ([H])[H]127. [H][*:1] [H]O[*:2] [H]Oc1c([H])c([H])c [H]Oc1c([H])c([H])c[H]O[*:5] (C([H])(O[*:3])C([H]) (C([H])(O[*:3])C([H])([H])C(═O)[*:4])c(O ([H])C(═O)[*:4])c(O [H])c1[H] [H])c1[H] 128.[H]O[*:1] [H][*:2] [H]c1c2c3c4c(c([H])n [H][*:4] [H]C([H])([H])O[*:5]([H])c4c1[H])C([H]) ([H])C([H])([H])N([H]) C(═O)C3([H])C([H]) ([*:3])O2129. [H][*:1] [H]Oc1c([H])c(O[H])c [H][*:3] [H]O[*:4][H]C([H])([H])O[*:5] (C(═O)/C(═C(\[H]) [*:2])C([H])([H])[H])c(O[H])c1[H] 130. [H]Oc1c([H])c([H])c [H]Oc1c([H])c([H])c [H]O[*:3][H]C([H])([H])O[*:4] [H][*:5] (C([H])(C([H])(C([H])(C([H])(C([H])(C([H]) ([H])O[H])C([H])(C([H]) ([H])O[H])C([H])([H])O[H])C([H]) (C([H])([H])O[H])C ([H])[*:1])[*:2])c ([H])([H])[*:1])([H])c1OC([H])([H]) [*:2])c([H])c1OC [H] ([H])([H])[H] 131.[H]c1c(OC([H])([H]) [H]O[*:2] [H]C([H])([H])O[*:3] [H][*:4][H]c1c(OC([H])([H])[H]) [H])c([H])c(OC([H]) c([H])c(OC([H])([H])[H])([H])[H])c(C([H])(O[*:5]) c(C([H])(O[*:5])C([H]) C([H])([H])C(═O)([H])C(═O)[*:1])c1OC([H]) [*:1])c1OC([H])([H])[H] ([H])[H] 132. [H][*:1][H]O/N═C(/c1c([H])c [H]C([H])([H])C([H]) [H]C([H])([H])C([H]) [H][*:5]([H])c([H])c(N([H])S ([H])O[*:3] ([H])O[*:4] (═O)(═O)[*:2])c1[H])N([H])[H] 133. [H]Oc1c([H])c([H])c [H][*:2] [H]C(═C([H])[*:4])C[H]C(═C([H])[*:4])C [H]Oc1c([H])c([H])c(C (C([H])(C([H])([H])(O[*:3])(C([H])([H]) (O[*:3])(C([H])([H]) ([H])(C([H])([H])O[*:5])CO[*:5])C([H])([H])[*:1]) [H])C([H])([H])[H] [H])C([H])([H])[H]([H])([H])[*:1])c(O[H])c1 c(O[H])c1C([H])([H])C C([H])([H])C([H])═C(C([H])═C(C([H]) ([H])([H])[H])C([H])([H]) ([H])[H])C([H]) [H] ([H])[H]134. [H]Oc1c([H])c([H])c [H]O[*:2] [H]C([H])([H])O[*:3][H]C(═C(C([H])([H]) [H]C([H])([H])O[*:5] (C(═O)C([H])([H])[*:1])[H])C([H])([H])[H])C c(O[H])c1[H] ([H])([H])[*:4] 135. [H]O[*:1][H][*:2] [H]Oc1c([H])c([H])c2 [H]Oc1c([H])c([H])c2 [H][*:5]c(c1[H])OC([H])([H]) c(c1[H])OC([H])([H]) C(O[H])([*:3])C2([H])OC(O[H])([*:3])C2([H])O [*:4] [*:4] 136. [H]Oc1c([H])c([H])c[H]Oc1c([H])c([H])c2c [H]C([H])([H])O[*:3] [H][*:4] [H]O[*:5]2c(c1[H])OC(C([H]) (c1[H])OC(C([H]) ([H])[H])(C([H])([H])([H])[H])(C([H]) [H])C([H])([H])C([H]) ([H])[H])C([H])([H])c(c(═O):[*:1]) ([H])C([H])([H])c c-2o:[*:2] (c(═O):[*:1])c-2o:[*:2]137. [H][*:1] [H]O[*:2] [H]C(═C(C([H])([H]) [H]C(═C(C([H])([H])[H]O[*:5] [H])C([H])([H])[H])C [H])C([H])([H])[H])C([H])([H])c1c([H])c(C ([H])([H])c1c([H])c(C ([H])(O[*:3])C([H])([H])(O[*:3])C([H]) ([H])C(═O)[*:4])c([H]) ([H])C(═O)[*:4])c([H])c(OC([H])([H])[H])c1 c(OC([H])([H])[H])c1 OC([H])([H])[H]OC([H])([H])[H] 138. [H]Oc1c([H])c([H])c [H][*:2] [H]O[*:3] [H][*:4][H]Oc1c([H])c([H])c(C (C([H])(C([H])([H]) ([H])(C([H])([H])O[*:5])CO[*:5])C([H])([H])[*:1]) ([H])([H])[*:1])c(OC([H]) c(OC([H])([H])[H])c1C([H])[H])c1C([H])([H])C ([H])([H])C([H])═C ([H])═C(C([H])([H])[H])C(C([H])([H])[H])C([H]) ([H])([H])[H] ([H])[H] 139. [H][*:1] [H]O[*:2][H]Oc1c([H])c([H])c [H]Oc1c([H])c([H])c [H]O[*:5] (C([H])(O[*:3])C([H])(C([H])(O[*:3])C([H]) (O[H])C([H])([H])[*:4])c (O[H])C([H])([H])([H])c1O[H] [*:4])c([H])c1O[H] 140. [H]Oc1c([H])c([H])c[H]Oc1c([H])c([H])c2c [H]C([H])═C(C([H]) [H]C([H])═C(C([H]) [H][*:5]2c(c1[H])OC([H])([*:1]) (c1[H])OC([H]) ([H])[H])C([H])(O[*:3])C([H])[H])C([H])(O[*:3])C C2(O[H])C([H])([H])O[*:2] ([*:1])C2(O[H])C([H])([H])[*:4] ([H])([H])[*:4] ([H])([H])O[*:2] 141. [H][*:1] [H]O[*:2][H][*:3] [H][*:4] [H]N(c1nc(C([H])([H]) [H])nc2sc3c(c12)C([H])([H])C([H])([H])C3([H]) [H])[*:5]

TABLE 2-C R1 R2 1. [H]O[*:1]•[H]c(:[*:1]):[*:3] [H][*:2] 2.[H]N([H])S(═O)(═O)N([H])c(c(OC([H])([H])[H]):[*:1]):[*:4]•[H][*:1][H][*:2] 3. [H]C([H])([H])[*:1]•[H]Oc(:[*:1]):[*:3] [H][*:2] 4.[H]O[*:1]•[H]Oc(c([H]):[*:1]):[*:4] [H][*:2] 5.[H]O[*:1]•[H]c(:[*:1]):[*:3] [H][*:2] 6.[H]N([H])S(═O)(═O)N([H])[*:1]•[H]N═C(c(:[*:1]):[*:3])N([H])[H] [H][*:2]7. [H]N([H])S(═O)(═O)N([H])c(:[*:1]):[*:3]•[H][*:1] [H][*:2] 8.[H]c(o:[*:1])c([H])c(═O)c(:[*:1]):[*:3] [H][*:2] 9.[H][*:1]•[H]c(:[*:1]):[*:3] [H][*:2] 10.[H]N═C(c(c(N([H])S(═O)(═O)N([H])[H]):[*:1]):[*:4])N([H])[H]•[H][*:1][H][*:2] 11. [H]O[*:1]•[H]Oc(c([H]):[*:1]):[*:4] [H][*:2] 12.[H]C(═O)[*:1]•[H]c(:[*:1]):[*:3] [H][*:2] 13.[H]O[*:1]•[H]Oc(c([H]):[*:1]):[*:4] [H][*:2] 14.[H]N([H])[*:1]•[H]O/N═C(/c(:[*:1]):[*:3])N([H])[H] [H][*:2] 15.[H]N([H])S(═O)(═O)N([H])c(:[*:1]):[*:3]•[H][*:1] [H][*:2] 16.[H][*:1]•[H]c(:[*:1]):[*:3] [H][*:2] 17.[H]N([H])S(═O)(═O)N([H])[*:1]•[H]c(:[*:1]):[*:3] [H][*:2] 18.[H][*:1]•[H][N:0]([H])[S:0](═[O:0])(═[O:0])[N:0]([H])[c:0](:[*:1]):[*:3][Cl:0][*:2] 19.[H][N:0]([H])[S:0](═[O:0])(═[O:0])[N:0]([H])[*:1]•[H][O:0]/[N:0]═[C:0](/[c:0](:[*:1]):[*:3])[N:0]([H])[H][H][*:2] 20. [H][*:1]•[H][N:0]([H])[c:0]([c:0]([Cl:0]):[*:1]):[*:4][Cl:0][*:2] 21. [H]c(n:[*:1])n([H])c(═O):[*:2]•o(:[*:1]):[*:4][H]c(n:[*:1])n([H])c(═O):[*:2] 22.F[*:1]•[H]N═C(c(:[*:1]):[*:3])N([H])[H] [H][*:2] R3 1.[H]O[*:3]•[H]c(:[*:1]):[*:3] 2. [H]N([H])[*:3]•[H]N═[*:3] 3.[H]O[*:3]•[H]Oc(:[*:1]):[*:3] 4. O═[*:3]•[H]C([H])([H])O[*:3] 5.[H]C([H])([H])[*:3]•[H]c(:[*:1]):[*:3] 6.[H]N═C(c(:[*:1]):[*:3])N([H])[H]•[H][*:3] 7.[H]N([H])S(═O)(═O)N([H])c(:[*:1]):[*:3]•[H]N═C(N([H])[H])[*:3] 8.[H]O[*:3]•[H]c(o:[*:1])c([H])c(═O)c(:[*:1]):[*:3] 9.[H]N([H])S(═O)(═O)N([H])[*:3]•[H]c(:[*:1]):[*:3] 10.[H][*:3]•[H][*:3]•[H][*:3] 11.O═[*:3]•[H]C([H])([H])C([H])(C([H])([H])[H])[*:3] 12.[H]O[*:3]•[H]c(:[*:1]):[*:3] 13. O═[*:3]•[H]C([H])([H])[*:3] 14.[H]O/N═C(/c(:[*:1]):[*:3])N([H])[H][H][*:3] 15.[H]N([H])S(═O)(═O)N([H])c(:[*:1]):[*:3]•[H]O/N═C(\N([H])[H])[*:3] 16.[H]N([H])S(═O)(═O)N([H])[*:3]•[H]c(:[*:1]):[*:3] 17.[H][*:3]•[H]c(:[*:1]):[*:3] 18.[H][N:0]([H])[S:0](═[O:0])(═[O:0])[N:0]([H])[c:0](:[*:1]):[*:3]•[H][O:0]/[N:0]═[C:0](\[N:0]([H])[H])[*:3]19. [H][*:3]•[H][O:0]/[N:0]═[C:0](/[c:0](:[*:1]):[*:3])[N:0]([H])[H] 20.[H][N:0]([H])[*:3]•[H][O:0][N:0]═[*:3] 21. [H][*:3]•[H][*:3]•[H][*:3]22. [H]N═C(c(:[*:1]):[*:3])N([H])[H]•[H][*:3] R4 R5 1. [H][*:4][H]O[*:5] 2. [H]N([H])S(═O)(═O)N([H])c(c(OC([H])([H])[H]):[*:1]):[*:4][H][*:5] 3. [H]C([H])([H])O[*:4] [H]O[*:5] 4. [H]Oc(c([H]):[*:1]):[*:4][H]O[*:5] 5. [H][*:4] [H]O[*:5] 6. F[*:4] [H][*:5] 7. F[*:4] [H][*:5] 8.[H][*:4] [H]O[*:5] 9. [H]N═C(N([H])[H])[*:4] [H][*:5] 10.[H]N═C(c(c(N([H])S(═O)(═O)N([H])[H]):[*:1]):[*:4])N([H])[H] [H][*:5] 11.[H]Oc(c([H]):[*:1]):[*:4] [H]O[*:5] 12. [H]C([H])([H])O[*:4] [H]O[*:5]13. [H]Oc(c([H]):[*:1]):[*:4] [H]O[*:5] 14. [H]C([H])([H])O[*:4][H]C([H])([H])O[*:5] 15. F[*:4] [H][*:5] 16. [H]O/N═C(/N([H])[H])[*:4][H][*:5] 17. [H]N═C(N([H])[H])[*:4] [H][*:5] 18. [H][*:4] [H][*:5] 19.[Br:0][*:4] [H][*:5] 20. [H][N:0]([H])[c:0]([c:0]([Cl:0]):[*:1]):[*:4][H][*:5] 21. o(:[*:1]):[*:4] [H]C([H])([H])[*:5] 22.[H]N([H])S(═O)(═O)N([H])[*:4] [H][*:5]

TABLE 2-D R1 R2 R3 R4 R5 R6 1. [H][*:1] [H][*:2] [H]C([H])([H])[H]C([H])([H]) [H]Oc1c([H])c([H]) O═[*:6]•[H]Oc1c([H]) O[*:3] O[*:4]c([H])c(:[*:6]) c([H])c([H])c(:[*:6]) c1n(C([H])([H])c1n(C([H])([H])[H]):[*:5] [H]):[*:5] 2. [H][*:1] [H]C([H])([H])[H]C([H])([H]) [H]C([H])([H]) [H]Oc1c([H])c([H]) O═[*:6]•[H]Oc1c([H])O[*:2] O[*:3] O[*:4] c([H])c(:[*:6]) c([H])c([H])c(:[*:6])c1n(C([H])([H]) c1n(C([H])([H])[H]):[*:5] [H]):[*:5] 3. [H][*:1][H]C([H])([H]) [H]C([H])([H]) [H]O[*:4] [H][*:5] [H][*:6]•[H][*:6]•[H]Oc1c2c(c(C(═O)[*:3]) Oc1c2c(c(C(═O)[*:3]) [*:6] c(C(═O)[*:2])c(C(═O)[*:2]) c1OC([H])([H])[H]) c1OC([H])([H])[H]) OC([H])([H])O2OC([H])([H])O2 4. [H][*:1] [H]c1c(OC([H])([H]) [H]c1c(OC([H])([H])[H]O[*:4] [H][*:5] [H][*:6]•[H][*:6]•[H] [H])c(OC([H])([H])[H])c(OC([H])([H]) [*:6] [H])c(OC([H])([H]) [H])c(OC([H])([H])[H])c(C(═O)[*:2]) [H])c(C(═O)[*:2]) c1C(═O)[*:3] c1C(═O)[*:3] 5.[H][*:1] [H][*:2] [H]O[*:3] [H]C([H])([H]) [H]Oc1c([H])c([H])O═[*:6]•[H]Oc1c([H]) O[*:4] c([H])c(:[*:6]) c([H])c([H])c(:[*:6])c1n(C([H])([H]) c1n(C([H])([H])[H]):[*:5] [H]):[*:5] 6. [H]Oc(c([H])[H]C([H])([H]) [H]C([H])([H]) [H]O[*:4] [H][*:5][H]Oc(c([H])c([H]):[*:6]) c([H]):[*:6]) O[*:2] O[*: 3]c(OC([H])([H])[H]) c(OC([H])([H]) c(:[*:1]):[*:6] [H])c(:[*:1]):[*:6] 7.[H]C([H]) [H][*:2] [H][*:3] [H]N([H])S(═O) [H][*:5][H]n(c(═O)c1c(n:[*:6]) ([H])C([H]) (═O)[*:4] c(C([H])([H])C([H])([H])C([H]) ([H])C([H])([H]) ([H])[*:1] [H])nn1C([H])([H]) [H]):[*:6] 8.[H][*:1] [H][*:2] [H]C([H])([H]) [H][*:4] [H]c1c2c(c(n(C([H])O═[*:6]•[H] O[*:3] ([H])[H]):[*:5]) c1c2c(c(n(C([H])([H])c(:[*:6])c1[H]) [H]):[*:5])c(:[*:6]) OC([H])([H])O2 c1[H])OC([H])([H])O29. [H]Oc(c(OC([H]) [H]C([H]) [H]C([H])([H]) [H]O[*:4] [H][*:5][H]Oc(c(OC([H])([H]) ([H])[H])c([H]) ([H])O[*:2] O[*:3] [H])c([H])c(:[*:1]):[*:6]) c(:[*:1]):[*:6]) c([H]):[*:6] c([H]):[*:6] 10.[H]Oc1c([H]) [H][*:2] [H]C([H])([H]) [H][*:4] [H]O[*:5] O═[*:6]•[H]c(O[H]) O[*:3] Oc1c([H])c(O[H]) c2c3c1OC(C([H]) c2c3c1OC(C([H])([H])[H]) ([H])[H])(C([H]) (C([H])([H]) ([H])[H])C3([H]) [H])C3([H])C([H])([H]) C([H])([H]) c(:[*:6])c-2:[*:1] c(:[*:6])c-2:[*:1] 11.[H][*:1] [H][*:2] [H]C([H])([H]) [H][*:4] [H]Oc1c([H])O═[*:6]•[H]Oc1c([H]) [*:3] c(O[H])c([*:6]) c(O[H])c([*:6])c(C([H])c(C([H])([H]) ([H])[*:5])c1[H] [*:5])c1[H] 12. [H][*:1][H]Oc1c(OC([H])([H]) [H]Oc1c(OC([H])([H]) [H][*:4] [H]C([H])[H]C([H])([H]) [H])c(C([H])([H]) [H])c(C([H])([H]) ([H])C(O[*:5])C(O[*:5])(C([H])([H]) C([H])([H])C(O[H]) C([H])([H])C(O[H] (C([H])([H])[H])C([H])([H]) (C([H])([H])[H]) )(C([H])([H])[H]) [H])C([H])[*:6]•[H][*:6]•[H] C([H])([H])[H]) C([H])([H])[H]) ([H])[*:6] [*:6]c(c(═O):[*:2])c(o:[*:3]) c(c(═O):[*:2]) c1[H] c(o:[*:3])c1[H] 13.[H]Oc1c([H]) [H]C1([H])OC([H]) [H]C1([H])OC([H]) [H][*:4] [H]C([H])([H])O═[*:6]•[H]Oc1c([H]) c([H])c([H]) (O[*:3])C([H])([*:2])(O[*:3])C([H])([*:2]) O[*:5] c([H])c([H])c(:[*:1]) c(:[*:1])c1:[*:6]C1([H])[H] C1([H])[H] c1:[*:6] 14. [H][*:1] [H]O[*:2] [H][*:3] [H]C([H])[H]C([H])(OC([H]) [H]Oc(c([H])c([H]):[*:6]) (OC([H])([H])([H])[*:5])C([H]) c(OC([H])([H])[H]) [*:5])C([H]) ([H])[*:4]c([H]):[*:6] ([H])[*:4] 15. [H]C(OC([H]) [H][*:2] [H]C([H])([H])[H]Oc1c([H]) [H]Oc1c([H])c([H]) [H]C(OC([H])([*:1]) ([*:1])[*:6])═CO[*:3] c([H])c([H]) c([H])c(o:[*:5]) [*:6])═C([H]) ([H])[*:6] c(o:[*:5])c1c(═O):[*:4] [*:6]•[H][*:6] c1c(═O):[*:4] 16. [H]C([H]) [H]O[*:2][H]C([H])([H]) [H]C([H])([H]) [H]Oc(c([H]) [H]Oc(c([H])c([H]):[*:6])([H])[*:1] O[*:3] O[*:4] c([H]):[*:6])c([H]) c([H])c(o:[*:5]):[*:6]c(o:[*:5]):[*:6] 17. [H][*:1] [H][*:2] [H]O[*:3] [H][*:4] [H]O[*:5]O═[*:6]•[H]Oc1c([H]) c([H])c([H])c([*:6]) c1[H] 18. [H][*:1][H]Oc1c(OC([H])([H]) [H]Oc1c(OC([H])([H]) [H][*:4] [H]C([H])([H])[H]C([H])([H])C(O[*:5]) [H])c(C([H])([H]) [H])c(C([H])([H])C(O[*:5])(C([H]) (C([H])([H])[H]) C([H])═C(C([H])([H]) C([H])═C(C([H])([H])[H])C([H]) C([H])([H])[*:6]•[H] [H])C([H])([H]) ([H])[H])C([H])([H])[*:6] [*:6]•[H][*:6] [H])c(c(═O):[*:2]) ([H])[H]) c(o:[*:3])C1[H]c(c(═O):[*:2]) c(o:[*:3])C1[H] 19. [H]C([H]) [H]O[*:2] [H][*:3][H]Oc1c(C([H]) [H]Oc1c(C([H]) [H]C(═C(C([H])([H]) ([H])[*:1] ([H])C([H])([H])C([H]) [H])C([H])([H])[H]) (O[H]) (O[H])C(═C([H])[*:6]•[H][*:6]•[H][*:6] C(═C([H]) [H])C([H]) [H])C([H])([H])[H])c(OC([H]) ([H])[H]) ([H])[H])c([H]) c(OC([H])([H]) c(o:[*:4])[H])c([H]) c1c(═O):[*:5] c(o:[*:4]) c1c(═O):[*:5] 20. [H][*:1] [H][*:2][H]C([H])([H]) [H][*:4] [H]Oc1c([H]) O═[*:6]•[H]Oc1c([H]) [*:3]c(O[H])c([*:6]) c(O[H])c([*:6])c(C([H]) c(C([H])([H]) ([H])[*:5])c1[H][*:5])c1[H] 21. [H]C([H]) [H][*:2] [H][*:3] [H]N1C([H])([H]) [H][*:5][H]n(c1c(C([H])([H]) ([H])C([H]) C([H])([H]) C([H])([H])C([H])([H])([H])[*:1] N(S(═O)(═O) [H])nn(C([H])([H]) [*:4])C([H])[H])c1c(═O)n:[*:6]):[*:6] ([H])C1([H]) [H] 22. [H][*:1] [H][*:2][H]C([H])([H]) [H]c1c(O[*:5]) [H]c1c(O[*:5]) O═[*:6]•[H][*:6] [*:3]c(OC(═O)[*:4]) c(OC(═O)[*:4]) c(C([H]) c(C([H])([H])[H]) ([H])[H])c2c1OC(C([H])([H]) c2c1OC(C([H]) [H])(C([H])([H]) ([H])[H])[H])C([H])([H]) (C([H])([H]) C2═O [H])C([H]) ([H])C2═O 23. [H][*:1][H][*:2] [H][*:3] [H]c1c(OC([H]) [H]O[*:5] [H]C([H])([H])C([H])([H])[H]) ([H])[*:6]•[H][*:6]•[H] c([*:4])c(OC([H]) [*:6]([H])[H])c([H]) c1C([H])([H])[H] 24. [H][*:1] [H][*:2] [H]O[*:3][H][*:4] [H]Oc1c([H])c([H]) O═[*:6]•[H]Oc1c([H]) c(:[*:6])c(o:[*:5])c([H])c(:[*:6])c(o:[*:5]) c1OC([H])([H])[H] c1OC([H])([H])[H] 25.[H]C([H]) [H]O[*:2] [H][*:3] [H]Oc(c([H]) [H]Oc(c([H])[H]Oc(c([H])c(C([H]) ([H])[*:1] c(C([H])([H]) c(C([H])([H])C([H])([H])C([H])(N([H]) C([H])(N([H]) (N([H])C([H])([H])C([H])([H])C([H])([H]) C([H])([H]) C([H])([H])[*:4]) [*:4])[*:5]):[*:6])C([H])([H]) [*:5]):[*:6]) c(OC([H])([H])[H]) [*:4]) c(OC([H])([H])c([H]):[*:6] [*:5]):[*:6]) [H])c([H]):[*:6] c(OC([H])([H])[H])c([H1):[*:6] 26. [H]C([H]) [H]O[*:2] [H][*:3] [H]C([H])([H])[H]Oc1c([H])c [H]C([H])([H])C(C([H]) ([H])C(C([H]) O[*:4] (OC([H])([H])([H])[H])([*:1]) ([H])[H]) [H])c([H]) [*:6]•[H]Oc1c([H]) ([*:1])[*:6]c2oc([*:5])c(C([H]) c(OC([H])([H])[H]) ([H])[*:6])c([H])c2oc([*:5])c(C([H]) c(═O)c12 ([H])[*:6]) c(═O)c12•[H][*:6] 27.[H]Oc1c([H]) [H][*:2] [H][*:3] [H]C([H])([H]) [H][*:5]O═[*:6]•[H]Oc1c([H]) c(O[H])c(:[*:6]) O[*:4] c(O[H])c(:[*:6])c(:[*:1])c1[H] c(:[*:1])c1[H] 28. [H][*:1] [H][*:2] [H]O[*:3] [H][*:4][H]Oc1c([H])c([H]) O═[*:6]•[H]Oc1c([H]) c([H])c(:[*:6])c([H])c([H])c(:[*:6]) c1n(C([H])([H]) c1n(C([H])([H])[H]):[*:5][H]):[*:5] 29. [H][*:1] [H]OC(O[*:3])(C([H]) [H]OC(O[*:3])(C([ [H][*:4][H]c(c(OC([H]) [H]C([H])([H]) ([H])[H])C([H]) H])([H])[H])C([H])([H])[H]) O[*:6]•[H]c(c(OC([H]) ([H])C(═O)[*:2] ([H])C(═O)[*:2]c([H]):[*:6]):[*:5] ([H])[H]) c([H]):[*:6]):[*:5] 30. [H][*:1] [H][*:2][H]O[*:3] [H][*:4] [H]Oc1c([H])c([H]) O═[*:6]•[H]Oc1c([H])c(:[*:6])c(n(C([H]) c([H])c(:[*:6])c(n(C([H]) ([H])[H]):[*:5])([H])[H]):[*:5]) c1OC([H])([H])[H] c1OC([H])([H])[H] 31. [H][*:1][H]OC([H])(C(═C([H]) [H]OC([H])(C(═C([H]) [H][*:4] [H]C([H])([H])[H]C(═C(C([H])([H]) [H])C([H])([H]) [H])C([H])([H]) O[*:5][H])C([H])([H])[H]) [H])C([H])([H]) [H])C([H])([H]) [*:6]•[H][*:6]•[H]c1c(OC([H])([H])[H]) c1c(OC([H])([H]) [*:6] c(OC([H])([H])[H])[H])c(OC([H])([H]) c([H])c(o:[*:3]) [H])c([H])c(o:[*:3]) c1c(═O):[*:2]c1c(═O):[*:2] 32. [H]Oc1c([H]) [H]O[*:2] [H][*:3] [H]O[*:4][H]C([H])([H]) O═[*:6]•[H]Oc1c c([H])c([H]) O[*:5] ([H])c([H])c([H])c(:[*:6])c1:[*:1] c(:[*:6])c1:[*:1] 33. [H][*:1] [H]c1c(OC([H])([H])[H]c1c(OC([H])([H]) [H]O[*:4] [H][*:5] [H][*:6]•[H][*:6]•[H][H])c(OC([H])([H]) [H])c(OC([H])([H]) [*:6] [H])c([H])c(C(═O)[H])c([H])c(C(═O) [*:3])c1C(═O)[*:2] [*:3])c1C(═O)[*:2] 34. [H][*:1][H][*:2] [H][*:3] [H]O[*:4] [H]Oc1c([H]) O═[*:6]•[H]Oc1c([H])c([*:6])c(C(═O) c([*:6])c(C(═O)[*:5]) [*:5])c(O[H]) c(O[H])c1OC([H])c1OC([H])([H]) ([H])[H] [H] 35. [H]C([H]) [H][*:2] [H]O[*:3] [H][*:4][H]Oc1c([H]) O═[*:6]•[H]Oc1c([H]) ([H])[*:1] c(C([H])([H])c(C([H])([H])O[H]) O[H])c([H]) c([H])c(C(═O)[*:5]) c(C(═O)[*:5]) c1[*:6]c1[*:6] 36. [H][*:1] [H]Oc1c(OC([H])([H]) [H]Oc1c(OC([H])([H]) [H][*:4][H]O[*:5] [H][*:6]•[H][*:6]•[H] [H])c(OC([H])([H]) [H])c(OC([H])([H])[*:6] [H])c([H])c(C(═O)[*:2]) [H])c([H])c(C(═O) c1C(═O)[*:3][*:2])c1C(═O)[*:3] 37. [H][*:1] [H][*:2] [H]C([H])([H])[*:3] [H][*:4][H]Oc1c([H]) O═[*:6]•[H]Oc1c([H]) c(O[H])c([*:6]) c(O[H])c([*:6])c(C(═O)c(C(═O)[*:5]) [*:5])c1[H] c1[H] 38. [H][*:1] [H][*:2][H]C([H])([H])O[*:3] [H][*:4] [H]Oc1c([H]) O═[*:6]•[H]Oc1c([H])c(C([H])([H]) c(C([H])([H])[H]) [H])c([H]) c([H])c(C(═O)[*:5])c(C(═O)[*:5]) c1[*:6] c1[*:6] 39. [H][*:1] [H]Oc1c2c(c(c(═O):[*:2]) [H][H][*:4] [H]C([H]) [H]C([H])([H])C(O[*:5]) c(o:[*:3])c1[H])Oc1c2c(c(c(═O): ([H])C(O[*:5]) (C([H])([H])[H]) C([H])([H])C([H])[*:2])c(o:[*:3]) (C([H])([H]) C([H])([H])[*:6]•[H] ([H])C(C([H])([H])c1[H])C([H])([H]) [H])C([H]) [*:6]•[H][*:6] [H])(C([H])([H])C([H])([H])C(C([H]) ([H])[*:6] [H])O2 ([H])[H])(C([H]) ([H])[H])O2 40.[H]C(OC([H]) [H][*:2] [H]C([H])([H]) [H]Oc1c([H]) [H]Oc1c([H])[H]C(OC([H])([*:1]) ([*:1]) O[*: 3] c(OC([H])([H]) c(OC([H])([H])[*:6])═C([H])[*:6]•[H] [*:6])═C([H]) [H])c(OC([H]) [H])c(OC([H]) [*:6][*:6] ([H])[H]) ([H])[H]) c(o:[*:5]) c(o:[*:5]) c1c(═O):[*:4]c1c(═O):[*:4] 41. [H][*:1] [H]Oc1c([H]) [H]Oc1c([H])c(C(═O) [H][*:4][H][*:5] [H][*:6]•[H][*:6]•[H] c(C(═O)[*:3])c(C(═O) [*:3])c(C(═O)[*:2])[*:6] [*:2])c(O[H])c1OC([H]) c(O[H])c1OC([H]) ([H])[H] ([H])[H] 42.[H]Oc1c(OC([H]) [H][*:2] [H]O[*:3] [H][*:4] [H]O[*:5]O═[*:6]•[H]Oc1c(OC([H]) ([H])[H]) ([H])[H])c([H]) c([H])c(:[*:6])c(:[*:6])c(:[*:1])c1[H] c(:[*:1])c1[H] 43. [H][*:1] [H]Oc(c([H])[H]Oc(c([H]) [H][*:4] [H]c(c(o:[*:5]) O═[*:6]•[H]c(c(o:[*:5])c(O[H]):[*:2]) c(O[H]):[*:2]) C([H])([H]) C([H])([H])[H]):[*:6]c([H]):[*:3] c([H]):[*:3] [H]):[*:6] 44. [H]C([H]) [H]O[*:2] [H][*:3][H]Oc1c(C([H]) [H]Oc1c(C([H]) [H]C(═C(C([H])([H]) ([H])[*:1] ([H]) ([H])[H])C([H])([H])[H]) C([H])═C(C([H]) C([H])═C(C([H])[*:6]•[H][*:6]•[H][*:6] ([H]) ([H])[H])C([H]) [H])C([H]) ([H])[H])([H])[H]) c(OC([H])([H]) c(OC([H])([H]) [H])c([H])c(o:[*:4]) [H])c([H])c1c(═O):[*:5] c(o:[*:4]) c1c(═O):[*:5] 45. [H]C([H]) [H]O[*:2][H]C([H])([H]) [H]C([H]) [H]Oc(c([H])c([H]) [H]Oc(c([H])c([H])([H])[*:1] O[*:3] ([H])O[*:4] c([H]):[*:6])c([H]):[*:6])c(o:[*:5]):[*:6] c(o:[*:5]):[*:6] 46. [H][*:1][H]C([H])([H]) [H]O[*:3] [H][*:4] [H]Oc1c([H])c([H])O═[*:6]•[H]Oc1c([H]) O[*:2] c([H])c(C(═O) c([H])c([H])c(C(═O)[*:5])[*:5])c1[*:6] c1[*:6] 47. [H]C([H]) [H]C([H])([H]) [H][*:3][H]Oc1c(C([H]) [H]Oc1c(C([H]) [H]C(═C(C([H])([H]) ([H])[*:1] O[*:2]([H])C([H]) ([H])C([H]) [H])C([H])([H])[H]) (O[H]) (O[H])C(═C([H])[*:6]•[H][*:6]•[H][*:6] C(═C([H]) [H])C([H]) [H]) ([H])[H])c(O[H])C([H])([H]) c(c(═O):[*:5]) [H])c(O[H]) c(o:[*:4])c1[H] c(c(═O):[*:5])c(o:[*:4])c1[H] 48. [H][*:1] [H]OC(O[*:3])(C([H]) [H]OC(O[*:3]) [H][*:4][H] [H]C([H])([H])O[*:6]•[H] ([H])[H])C([H]) (C([H])([H])Oc(c([H]):[*:5]) Oc(c([H]):[*:5])c([H]):[*:6] ([H])C(═O)[*:2] [H])C([H])c([H]):[*:6] ([H])C(═O)[*:2]

TABLE 2-E R1 R2 R3 R4 R5 R6 1. [H]Oc1c([H]) [H]O[*:2] [H][*:3] [H][*:4][H]O[*:5] [H]C([H]) c(O[H])c([H]) ([H])O[*:6] c(C([H])═[*:1])c1[H]•[H][*:1] 2. O═[*:1]•[H] [H][*:2] [H]Oc1c([H]) [H]O[*:4] [H][*:5][H]O[*:6] Oc1c([H])c([H]) c([H])c(C2([H]) c(C2([H])Oc3c([H])Oc3c([H])c([H]) c([H])c(C([H])(O[*:3]) c(C([H])(O[*:3])C([H])(O[H])[*:1]) C([H])(O[H]) c([H])c3OC2([H]) [*:1])c([H])C([H])([H]) c3OC2([H])C([H]) O[H])c([H]) ([H])O[H]) c1OC([H])([H])[H]c([H])c1OC([H]) ([H])[H] 3. [H]Oc1c([H])c([H]) [H]C([H]) [H][*:3][H][*:4] [H][*:5] [H]O[*:6] c(C2([H])OC([H]) ([H])O[*:2] ([H])C([H])([*:1])C2(O[H]) C([H])([H]) O[*:1])c([H]) c1OC([H])([H]) [H]•[H][*:1] 4.O═[*:1]•[H] [H][*:2] [H]Oc1c([H]) [H]O[*:4] [H][*:5] [H]O[*:6]Oc1c([H])c([H]) c([H])c(C2([H]) c(C2([H])Oc3c(O[H]) Oc3c(O[H])c([H])c([H])c([H]) c([H])c(C([H]) c(C([H])(O[*:3]) (O[*:3])C([H]) C([H])(O[H])(O[H])[*:1]) [*:1])c3C2([H]) c3C2([H])C([H]) C([H])([H])O[H]) ([H])O[H])c([H])c1OC([H]) c([H])c1OC([H]) ([H])[H] ([H])[H] 5. O═[*:1]•[H][H][*:2] [H]Oc1c([H])c [H]O[*:4] [H][*:5] [H]O[*:6] Oc1c([H])c([H])([H])c(C2([H]) c(C2([H])Oc3c(O[H]) Oc3c(O[H])c([H]) c([H])c(C([H])c(C([H])(O[*:3]) (O[*:3])C([H]) C([H])([H])[*:1]) ([H])[*:1])c([H])c3C2([H]) c ([H])c3C2([H]) C([H])([H])O[H]) C([H])([H])c([H])c1OC([H]) O[H])c([H]) ([H])[H] c1OC([H])([H]) [H] 6. [H]OC(═C([H])[H]C([H]) [H][*:3] [H][*:4] [H][*:5] [H]O[*:6] C(═O)C([H])([H])([H])O[*:2] [*:1])C([H])═C([H]) c1c([H])c([H]) c(O[H])c(OC([H])([H])[H])c1[H]•[H] [*:1]•[H][*:1] 7. [H]Oc1c([H])c([H]) [H]C([H])[H][*:3] [H][*:4] [H][*:5] [H]O[*:6] c(C2([H])Oc3c(OC([H]) ([H])O[*:2]([H])[H])c([H]) c(C([H])([H]) C4([H])C(═O) OC([H])([H])C4([H])[*:1])c([H]) c3C2([H])C([H]) ([H])O[H])c([H]) c1OC([H])([H])[H]•[H][*:1]•[H] [*:1] 8. O═[*:1]•[H] [H][*:2] [H]O[*:3][H]Oc1c([H])c([H]) [H][*:5] [H]O[*:6] Oc1c([H])c([H])c(C2([H])Oc3c(O[H]) c(C2([H])Oc3c(O[H]) c([H])c([H])c(C([H])c([H])c([H]) (O[*:4])C([H]) c(C([H])(O[*:4]) ([H])[*:1])c3C2([H])C([H])([H])[*:1]) C([H])([H])O[H]) c3C2([H])C([H])([H]) c([H])c1OC([H])O[H])c([H])c1OC([H]) ([H])[H] ([H])[H] 9. [H]OC(═C([H]) [H]C([H])[H][*:3] [H][*:4] [H][*:5] [H]O[*:6] C(═O)C([H])([H]) ([H])O[*:2][*:1])C([H])([H]) C([H])([H])c1c([H]) c([H])c(O[H]) c(OC([H])([H])[H])c1[H]•[H] [*:1]•[H][*:1] 10. [H]Oc1c([H]) [H][*:2] [H][*:3] [H][*:4][H]O[*:5] [H]C([H]) c(C([H]) ═[*:1])c([H]) ([H])O[*:6]c(C([H])([H])O[H]) c1OC([H])([H]) [H]•[H][*:1] 11. O═[*:1]•[H] [H][*:2][H]O[*:3] [H]Oc1c([H])c([H]) [H][*:5] [H]O[*:6] Oc1c([H])c([H])c(C2([H])C3([H]) c(C2([H])C3([H]) C(═O)C4(O[H]) C(═O)C4(O[H])OC([H])([H])C2([H]) OC([H])([H]) C4([H])C([H])(C([H]) C2([H])C4([H])(O[*:4])C([H])([H]) C([H])(C([H]) [*:1])C3([H])[H]) (O[*:4])C([H])c([H])c1OC([H])([H]) ([H])[*:1]) [H] C3([H])[H]) c([H])c1OC([H])([H])[H] 12. [H]Oc1c([H]) [H]Oc1c([H])c([H]) [H][*:3] [H][*:4] [H][*:5][H]Oc1c([H])c([H]) c(O[H])c(C(═O) c(C([H])(O[*:2]) c(C([H])(O[*:2])C([H])(O[H]) C([H])(O[*:6])C([H]) C([H])(O[*:6]) [*:1])c(O[*:1])([H])O[H])c([H]) C([H])([H])O[H]) c1[H]•[H][*:1] c1OC([H])([H])[H]c([H])c1OC([H]) ([H])[H] 13. [H]Oc1c([H]) [H]Oc1c([H])c([H]) [H][*:3][H][*:4] [H][*:5] [H]Oc1c([H])c([H]) c(O[H])c(C(═O) c(C([H])(O[*:2])c(C([H])(O[*:2]) C([H])(O[H]) C([H])(O[*:6]) C([H])(O[*:6])[*:1])c(O[*:1]) C([H])([H])O[H]) C([H])([H])O[H]) c1[H]•[H][*:1]c([H])c1OC([H]) c([H])c1OC([H]) ([H])[H] ([H])[H] 14. [H]Oc1c([H])c([H])[H]C([H]) [H][*:3] [H][*:4] [H][*:5] [H]O[*:6] c(C([H])([H])/([H])O[*:2] C([H])═C(/[H]) C(═O)C([H]) ([H])C(═O)/C ([H])═C(\[H])[*:1])c([H]) c1OC([H])([H]) [H]•[H] [*:1]•[H][*:1] 15. [H][*:1]•[H][H]c1c([H])c(N([H]) [H][*:3] [H]C([H]) [H]C([H]) [H][*:6] [*:1]•[H][*:1]S(═O)(═O)[*:2]) ([H])O[*:4] ([H])[*:5] c([H])c2c1N([H])C(═O)C(C([H])([H]) [H])(C([H])([H]) [H])C([H])([H])O2 16. O═[*:1]•[H][H][*:2] [H]Oc1c([H]) [H]O[*:4] [H][*:5] [H]O[*:6] Oc1c([H])c([H])c([H])c(C2([H]) c(C2([H])C3([H]) C3([H])C(═O) C(═O)C4(O[H])C4(O[H])OC([H]) OC([H])([H])C2([H]) ([H])C2([H])C4([H])C4([H])C([H])(C([H]) C([H])(C([H]) (O[*:3])C([H]) (O[*:3])C([H])(O[H])[*:1]) (O[H])[*:1]) C3([H])[H]) C3([H])[H]) c([H])c1OC([H])c([H])c1OC([H]) ([H])[H] ([H])[H] 17. [H]Oc1c([H]) [H]Oc1c([H])c([H])[H][*:3] [H][*:4] [H][*:5] [H]Oc1c([H])c([H]) c(O[H])c(C(═O)c(C([H])(O[*:6]) c(C([H])(O[*:6]) C([H])([H])[*:1]) C([H])(O[*:2])C([H])C([H])(O[*:2]) c(O[*:1])c1[H]•[H] ([H])O[H])c([H]) C([H])([H])O[H])[*:1] c1OC([H])([H])[H] c([H])c1OC([H]) ([H])[H] 18. O═S(═O)(N═[*:1])[H][*:2] O═S(═O) [H][*:4] [H][*:5] [H][*:6] [*:3]•[H]c1c([H]) (N═[*:1])c(S(═O)(═O)N([H]) [*:3] c2c([H])c(C([H]) ([H])[H])c([H]) c([H])c2C([H])([H])[H])c([H]) c([H])c1N([H]) [*:1] 19. [H][*:1]•[H][H]c1c([H])c(N([H]) [H][*:3] [H]C([H]) [H]C([H]) [H][*:6] [*:1]•[H][*:1]S(═O)(═O)[*:2]) ([H])C([H]) ([H])[*:5] c([H])c2c1N([H]) ([H])O[*:4]C(═O)C(C([H])([H]) [H])(C([H])([H]) [H])C([H])([H])O2 20. [H][*:1]•[H][H]c1c([H])c(N([H]) [H][*:3] [H]C([H]) [H]C([H]) [H][*:6] [*:1]•[H][*:1]S(═O)(═O)[*:2]) ([H])O[*:4] ([H])[*:5] c([H])c2c1OC([H])([H])C(C([H])([H]) [H])(C([H])([H]) [H])C(═O)N2[H] 21. [H][*:1]•[H][H]c1c([H])c(N([H]) [H][*:3] [H]C([H]) [H]C([H]) [H][*:6] [*:1]•[H][*:1]S(═O)(═O)[*:2]) ([H])C([H]) ([H])[*:5] c([H])c2c1OC([H]) ([H])O[*:4]([H])C(C([H])([H]) [H])(C([H])([H]) [H])C(═O)N2[H] 22. [H][*:1]•[H][H]c1c([H])c(N([H]) [H][*:3] [H]C([H]) [H][*:5] [H][*:6] [*:1]•[H][*:1]S(═O)(═O)[*:2]) ([H])O[*:4] c([H])c2c1OC([H]) ([H])C(C([H])([H])[H])(C([H])([H]) [H])C(═O)N2[H] 23. [H]Oc1c([H]) [H]C([H]) [H][*:3][H][*:4] [H][*:5] [H]O[*:6] c([H])c(C2([H]) ([H])O[*:2] OC([H])([H])C([H])([*:1])C2(OC(═O) C([H])([H])[H]) C([H])([H])O[*:1])c([H])c1OC([H]) ([H])[H]•[H][*:1] 24. [H]Oc1c([H]) [H]C([H]) [H][*:3][H][*:4] [H][*:5] [H]O[*:6] c([H])c(C([H]) ([H])O[*:2]([H])C2(O[H])C(═O) OC([H])([H])C2([H]) [*:1])c([H]) c1OC([H])([H])[H]•[H][*:1]•[H] [*:1] 25. [H]Oc1c([H])c([H]) [H]C([H]) [H][*:3][H][*:4] [H][*:5] [H]C([H]) c([C@@]2([H]) (O[*:2])O[*:6] (O[*:2])O[*:6]OC([H])([H]) C([H])([*:1]) C2([H])C([H]) ([H])O[*:1])c([H])c1O[H]•[H][*:1] 26. [H]Oc1c([H]) [H]C([H]) [H][*:3] [H][*:4] [H][*:5][H]O[*:6] c([H])c(C([H]) ([H])O[*:2] ([H])C([H])(C([H])([H])O[*:1])C([H]) (C([H])([H])O[H]) [*:1])c([H]) c1OC([H])([H])[H]•[H][*:1] 27. [H][*:1]•[H] [H][*:2] [H][*:3] [H][*:4] [H][*:5][H]c1c([H])c([H]) [*:1]•[H][*:1] c(/C(═N/S(═O)(═O) [*:6])N([H])c2c([H])c([H])c3c(c2[H]) n([H])c(═O)n3[H]) c([H])c1[H] 28. [H]Oc1c([H])[H]Oc1c([H])c([H]) [H][*:3] [H][*:4] [H]O[*:5] [H]Oc1c([H])c([H])c(O[H])c(C(═O) c(C([H])(O[*:6]) c(C([H])(O[*:6]) C([H])(O[H])C([H])(C([H])([H]) C([H])(C([H])([H]) [*:1])c(O[*:1]) O[H])[*:2])c([H])O[H])[*:2])c([H]) c1[H]•[H][*:1] c1OC([H])([H])[H] c1OC([H])([H])[H] 29.[H]OC(═O)[C@@] [H][*:2] [H]O[*:3] [H]OC(═O)[C@@] [H][*:5] [H]O[*:6]1([H])O[C@@] 1([H])O[C@@]([H]) ([H])(Oc2c([H]) (Oc2c([H])c([C@@]c([C@@]([H]) ([H])(O[*:4])[C@] (O[*:4])[C@] ([H])(O[H])[*:1])([H])(O[H])[*:1]) c([H])c([H])c2OC([H]) c([H])c([H])c2OC([H])([H])[H])[C@] ([H])[H])[C@] ([H])(O[H])[C@@] ([H])(O[H])[C@@]([H])(O[H])[C@] ([H])(O[H])[C@] 1([H])O[H] 1([H])O[H]•[H] [*:1]•[H][*:1]30. [H]Oc1c([H])c([H]) [H]C([H]) [H][*:3] [H][*:4] [H][*:5] [H]O[*:6]c(C([H])([H]) ([H])O[*:2] C2([H])C(═O)OC([H]) ([H])C2([H]) [*:1])c([H])c1OC([H])([H]) [H]•[H][*:1]•[H] [*:1] 31. [H][*:1]•[H] [H][*:2] [H][*:3][H][*:4] [H][*:5] [H]c1c([H])c([H]) [*:1]•[H][*:1] c(/C(═N\S(═O)(═O)[*:6])N([H])c2c([H]) c([H])c3c(c2[H]) n([H])c(═O)n3[H]) c([H])c1[H] 32.[H]Oc1c([H]) [H]C([H]) [H][*:3] [H][*:4] [H][*:5] [H]O[*:6]c([H])c(C([H]) ([H])O[*:2] ([H])C([H])(C([H]) ([H])O[*:1])C([H])(C([H])([H])O[H]) [*:1])c([H])c1OC([H]) ([H])[H]•[H][*:1] 33.[H]O[*:1]•[H] [H]C([H]) [H][*:3] [H][*:4] [H][*:5] [H]O[*:6]Oc1c([H])c([H]) ([H])O[*:2] c(C([H])([H])C2([H]) C([H])([H])OC(═O)C2([H])C([H]) ([H])c2c([H])c([H]) c(OC([H])(C([H]) ([H])O[H])[*:1])c(OC([H])([H]) [H])c2[H])c([H]) c1OC([H])([H]) [H]•[H][*:1] 34.[H][*:1]•[H] [H]c1c([H])c(N([H]) [H][*:3] [H]C([H])([H]) [H][*:5][H][*:6] [*:1]•[H][*:1] S(═O)(═O)[*:2]) C([H])([H])O[*:4]c([H])c2c1N([H]) C(═O)C(C([H])([H ])[H])(C([H])([H]) [H])C([H])([H])O235. [H][*:1]•[H] [H]c1c([H])c(N([H]) [H][*:3] [H]C([H])([H]) [H][*:5][H][*:6] [*:1]•[H][*:1] S(═O)(═O)[*:2]) C([H])([H])C([H])c([H])c2c1N(C([H]) ([H])O[*:4] ([H])[H])C(═O) C(C([H])([H])[H])(C([H])([H])[H]) C([H])([H])O2 36. [H]Oc1c([H]) [H]C([H])([H]) [H][*:3][H][*:4] [H][*:5] [H]O[*:6] c([H])c(C2([H]) O[*:2] OC([H])([H])C([H])([*:1])C2([H])C([H]) ([H])O[*:1])c([H]) c1OC([H])([H]) [H]•[H][*:1] 37.[H]Oc1c([H])c([H]) [H][*:2] [H][*:3] [H][*:4] [H]C([H]) [H]C([H])c(C2([H])OC([H]) (O[*:5])O[*:6] (O[*:5])O[*:6] ([H])C([H])([*:1])C2([H])C([H]) ([H])O[*:1])c([H]) c1OC([H])([H]) [H]•[H][*:1] 38.[H]Oc1c([H])c([H]) [H][*:2] [H][*:3] [H][*:4] [H]C([H]) [H]C([H])c(C2([H])OC([H]) (O[*:5])O[*:6] (O[*:5])O[*:6] ([H])C([H])([*:1])C2([H]) C([H])([H])O[*:1]) c([H])c1OC([H]) ([H])[H]•[H][*:1] 39.[H][*:1]•[H] [H]C([H])═C([H]) [H][*:3] [H]C([H]) [H][*:5] [H][*:6][*:1]•[H][*:1] C([H])([H])N1C(═O) ([H])O[*:4] C(C([H])([H])[H])(C([H])([H])[H]) C([H])([H])Oc2c([H]) c(N([H])S(═O) (═O)[*:2])c([H])c([H])c21 40. [H]N([H]) [H][*:2] [H][*:3] [H][*:4] [H][*:5] [H]C([H])[*:1]•[H]c1c([H]) ([H])[*:6] c(S(═O)(═O)N═[*:1]) c([H])c([H])c1C([H])([H])[H] 41. O═[*:1]•[H]Oc1c([H]) [H]Oc1c(C([H]) [H]Oc1c([H]) [H]O[*:4][H][*:5] [H]Oc1c(C([H]) c([H])c([H]) (C([H])(O[*:6]) c([H])c([H])(C([H])(O[*:6]) c(:[*:1])c1n(C([H]) C(O[H])(C([H])([H])c(:[*:1])c1n(C([H]) C(O[H])(C([H])([H]) ([H])[H]):[*:3][H])C([H])([H])[H]) ([H])[H]):[*:3] [H])C([H])([H]) [*:2])c(OC([H])([H])[H])[*:2])c(OC([H]) [H])c([H])c2c1c(═O) ([H])[H])c([H]) c1c([H])c([H])c2c1c(═O)c1c([H]) c(OC([H])([H])[H]) c([H])c(OC([H])([H])[H])c(OC([H])([H]) c(OC([H])([H])[H]) [H])c1n2[H] c1n2[H] 42.[H]N([H])[*:1]•[H] [H][*:2] [H][*:3] [H][*:4] [H][*:5] [H]N(S(═O)(═O)c1c([H])c([H])c(N([H]) C([H]) C(═O)ON═[*:1]) ([H])[H])[*:6] c([H])c1[H]43. [H]OC([H])([H]) [H]Oc1c([H])c([H]) [H][*:3] [H]O[*:4] [H]C([H])[H][*:6] [*:1]•[H]Oc1c([H]) c(C([H])([H])C2([H]) ([H])O[*:5]c([H])c(C(═O) C(═O)OC([H])([H]) [*:1])c([H])c1OC([H]) C2([H])C([H])([H])([H])[H]•[H][*:1] [*:2])c([H])c1OC([H]) ([H])[H] 44.O═[*:1]•[H]Oc1c([H]) [H]Oc1c(C([H])(C([H]) [H]Oc1c([H]) [H]O[*:4][H][*:5] [H]Oc1c(C([H]) c([H])c(:[*:1]) (O[*:6])C(O[H])(C([H])c([H])c(:[*:1]) (C([H])(O[*:6]) c(n(C([H])([H]) ([H])[H])C([H])([H])c(n(C([H])([H]) C(O[H])(C([H]) [H]):[*:3])c1OC([H]) [H])[*:2])c(OC([H])[H]):[*:3]) ([H])[H])C([H]) ([H])[H] ([H])[H])c([H]) c1OC([H])([H])[H]([H])[H])[*:2]) c2c1c(═O)c1c([H]) c(OC([H])([H])[H]) c([H])c(OC([H])c([H])c2c1c(═O) ([H])[H])c(OC([H]) c1c([H])c([H]) ([H])[H])c1n2[H]c(OC([H])([H])[H]) c(OC([H])([H]) [H])c1n2[H] 45. [H][*:1]•[H][H]c1c([H])c(N([H]) [H][*:3] [H]C([H]) [H][*:5] [H][*:6] [*:1]•[H][*:1]S(═O)(═O)[*:2]) ([H])C([H]) c([H])c2c1OC([H]) ([H])C([H])([H])C(C([H])([H]) ([H])O[*:4] [H])(C([H])([H]) [H])C(═O)N2[H] 46.[H]C(═O) [H][*:2] [H][*:3] [H][*:4] [H]Oc1c([H]) [H]Oc1c([H])c([H])C([H])═[*:1]•[H] c([H])c(C2([H]) c(C2([H])Oc3c([H]) [*:1]Oc3c([H])c([H]) c([H])c(C([H]) c(C([H])(O[*:5]) (O[*:5])C([H])C([H])(O[*:6]) (O[*:6])C([H]) C([H])([H]) ([H])O[H])c([H]) O[H])c([H])c3OC2([H])C([H]) c3OC2([H]) ([H])O[H])c([H]) C([H])([H])O[H]) c1O[H]c([H])c1O[H] 47. O═[*:1]•[H] [H][*:2] [H][*:3] [H]Oc1c([H]) [H]Oc1c([H])[H]Oc1c([H])c([H]) Oc1c([H])c(OC([H]) c(OC([H])([H]) c([H])c2c([H])c2c([H])c([H]) ([H])[H])c([H]) [H])c([H]) c([H])c(═O) c(═O)oc2c1/c(n(C([H])([H]) c(n(C([H])([H]) oc2c1/ C([H])═C(\[H])[H]):[*:4])c1:[*:1] [H]):[*:4])c1:[*:1] C([H])═C(\[H])C(O[*:6])(C([H])([H]) C(O[*:6])(C([H]) [H])C([H])([H]) ([H])[H])C([H])O[*:5] ([H])O[*:5] 48. [H]Oc1c([H])c([H]) [H][*:2] [H][*:3] [H][*:4][H]O[*:5] [H]C([H]) c(/C([H])═C(\[H]) ([H])O[*:6] C(═O)N([H])C([H])([H])[*:1])c([H]) c1OC([H])([H]) [H]•[H] [*:1]•[H][*:1] 49.[H]N(C([H])([H]) [H][*:2] [H][*:3] [H][*:4] [H][*:5] [H][*:6][H])[*:1]•[H] c1c([H])c([N+] (═O)[O—])c([H]) c(S(═O)(═O)N═[*:1]) c1[H]

The materials used in preparing the compounds of the invention, e.g.,the various structural subclasses and species of the compounds or thesynthetic precursors of the present compounds, are known compounds, orcan be synthesized by known methods described in the literature, or arecommercially available from various sources well known to those ofordinary skill in the art. These sources can be, for example,Sigma-Aldrich Corporation of St. Louis, Mo. USA and their subsidiariesFluka and Riedel-de Haen, at their various other worldwide offices, andother well-known chemical suppliers such as Fisher Scientific, TCIAmerica of Philadelphia, Pa., ChemDiv of San Diego, Calif., Chembridgeof San Diego, Calif., Asinex of Moscow, Russia, SPECS/BIOSPECS of theNetherlands, Maybridge of Cornwall, England, Acros, TimTec of Russia,Comgenex of South San Francisco, Calif., and ASDI Biosciences of Newark,Del.

The skilled artisan in the art of organic chemistry can readily carryout the synthesis of many starting materials and subsequentmanipulations without further direction. These include, for example,reduction of carbonyl compounds to their corresponding alcohols;oxidations; acylations; aromatic substitutions; both electrophilic andnucleophilic; etherifications; esterification; saponification;nitrations; hydrogenations; reductive animation and the like. Thesemanipulations are discussed in standard texts such as March's AdvancedOrganic Chemistry (3d Edition, 1985, Wiley-Interscience, New York),Feiser and Feiser's Reagents for Organic Synthesis, and in the variousvolumes and editions or Methoden der Organischen Chemie (Houben-Weyl),and the like. Many general methods for preparation of materialscomprising variously substituted heterocyclic, hetereoaryl, and arylrings (the precursors of Ar, hAr1, and/or hAr2) can be found in Methodender Organischen Chemie (Houben-Weyl), whose various volumes and editionsare available from Georg Thieme Verlag, Stuttgart. The entiredisclosures of the treatises recited above are hereby incorporated byreference in their entireties for their teachings regarding methods forsynthesizing organic compounds and their precursors.

The skilled artisan will also readily appreciate that certain reactionsare best carried out when other functionality is masked or protected inthe molecule, thus avoiding any undesirable side reactions and/orincreasing the yield of the reaction. Often the skilled artisan utilizesprotecting groups to accomplish such increased yields or to avoid theundesired reactions. These reactions are found in the literature and arealso well within the scope of the skilled artisan. Examples of many ofthese manipulations can be found for example in T. Greene and P. Wuts,Protecting Groups in Organic Synthesis, 3r Ed., John Wiley & Sons(1999).

Use of the Compounds of the Subject Invention to Enhance Sweeteners

The compounds of Table 1 and Table 2 (e.g., the compounds of Table 3),and derivatives thereof, can be used for one or more methods of thepresent invention. In one embodiment, the method can include increasingor enhancing sweet flavor. In another embodiment, the method can includemodulating a sweet receptor and/or its ligand.

According to the present invention, a method of modulating achemosensory receptor and/or its ligand can include modulating theactivity, structure, function, expression, and/or modification of achemosensory receptor as well as modulating, treating, or takingprophylactic measure of a condition, e.g., physiological or pathologicalcondition, associated with a chemosensory receptor.

In general, the compounds of the present invention, individually or incombination, can be provided in a composition, such as, for example, aningestible composition. In one embodiment, the compounds of the subjectinvention impart a more sugar-like temporal profile and/or flavorprofile to a sweetener composition by combining one or more of thecompounds with one or more sweeteners in a sweetener composition. Inanother embodiment, the compounds increase or enhance the sweet taste ofa composition. In another embodiment, the compounds can be in acomposition that modulates the sweet receptors and/or their ligandsexpressed at a place in the body other than in the taste buds.

The compounds or combination of compounds selected from Table 1 andTable 2 (e.g., the compounds of Table 3) should preferably be comestiblyacceptable, e.g., deemed suitable for consumption in food or drink, fromthe perspective of giving the comestible compositions an improved and/orpleasing sweet taste, and are not toxic and do not cause unpleasant orundesirable pharmacological or toxicological effects on a human or otheranimal at the typical concentrations they are employed as flavoringagents for the comestible compositions.

One of the methods of demonstrating that a flavorant compound iscomestibly acceptable is to have the compound tested and/or evaluated byan Expert Panel of the Flavor and Extract Manufacturers Association(FEMA) and declared as to be “Generally Recognized As Safe” (“GRAS”).The FEMA/GRAS evaluation process for flavorant compounds is complex butwell known to those of ordinary skill in the food product preparationarts, as is discussed by Smith, et al. in an article entitled “GRASFlavoring Substances 21,” Food Technology, 57(5), pgs 46-59, May 2003,the entire contents of which are hereby incorporated herein byreference.

In addition to the FEMA expert panel, an independent, qualified panel ofexperts in pertinent scientific disciplines may be formed by themanufacturer to evaluate the safety of a specific compound for GRASstatus. This process is known as a “self-determination of GRAS status.”

Another method of demonstrating that a flavorant compound is comestiblyacceptable is to obtain favorable review by the WHO/FAO Joint ExpertCommittee on Food Additives, or JECFA. There are also other evaluationmethods, such as independent review by the regulatory agency, which aregenerally known to those of ordinary skill in the food productpreparation arts.

In one embodiment, the compounds of the present invention can be used atconcentrations within acceptable oral toxicity levels. In anotherembodiment, the compounds of the present invention can be used at ligandenhancing concentrations, e.g., very low concentrations on the order ofa few parts per million, in combination with one or more knownsweeteners, natural or artificial, so as to reduce the concentration ofthe known sweetener required to prepare an ingestible composition havingthe desired degree of sweetness.

The compounds can be used to enhance the sweet taste or perception ofsweet taste of any suitable caloric, low-caloric, or non-caloricsweetener. Non-limiting examples of such sweeteners include caloriccarbohydrate sweeteners (including polyols), natural high-potencysweeteners, synthetic high-potency sweeteners, and combinations thereof.

As used herein, the phrase “natural high-potency sweetener” or “NHPS”means any sweetener found in nature, which may be in raw, extracted,purified, or any other form, singularly or in combination thereof andcharacteristically having a sweetness potency greater than sucrose,fructose, or glucose, but having fewer calories. Non-limiting examplesof NHPSs include rebaudioside A, rebaudioside B, rebaudioside C,rebaudioside D, rebaudioside E, rebaudioside F, dulcoside A, dulcosideB, rubusoside, stevia, stevioside, mogroside IV, mogroside V, Luo HanGuo sweetener, siamenoside, monatin and its salts (monatin SS, RR, RS,SR), curculin, glycyrrhizic acid and its salts, thaumatin, monellin,mabinlin, brazzein, hernandulcin, phyllodulcin, glycyphyllin,phloridzin, trilobatin, baiyunoside, osladin, polypodoside A,pterocaryoside A, pterocaryoside B, mukurozioside, phlomisoside I,periandrin I, abrusoside A, and cyclocarioside I.

As used herein, the phrase “synthetic sweetener” or “synthetichigh-potency sweetener” refers to any composition that is not found innature and that has a sweetness potency greater than sucrose, fructose,or glucose, yet has fewer calories. Non-limiting examples of syntheticsweeteners include sucralose, acesulfame potassium or other salts,aspartame, alitame, saccharin, neohesperidin dihydrochalcone, cyclamate,neotame,N-[3-(3-hydroxy-4-methoxyphenyl)propyl]-L-α-aspartyl]-L-phenylalanine1-methyl ester,N-[3-(3-hydroxy-4-methoxyphenyl)-3-methylbutyl]-L-α-aspartyl]-L-phenylalanine1-methyl ester,N-[3-(3-methoxy-4-hydroxyphenyl)propyl]-L-α-aspartyl]-L-phenylalanine1-methyl ester, salts thereof, and the like.

According to the present invention, NHPS and synthetic sweeteners can beused individually or in combination with other NHPSs and/or syntheticsweeteners. For example, the sweetener composition can comprise a singleNHPS or a single synthetic sweetener; a single NHPS in combination witha single synthetic sweetener; one or more NHPSs in combination with asingle synthetic sweeteners; a single NHPS in combination with one ormore synthetic sweeteners; or one or more NHPSs in combination with oneor more synthetic sweeteners. A plurality of NHPSs and/or syntheticsweeteners can be used so long as the combined effect does not adverselyaffect the taste of the sweetener composition or orally sweetenedcomposition.

In one embodiment, the present compounds can enhance the sweetness of asweetener under a broad range of pH, e.g., from acid pH to basic pH. ThepH can be, for example, from about 2.5 to about 9.0; from about 2.5 toabout 8.0; from about 2.8 to about 7.5; from about 3.0 to about 7, andfrom about 3.5 to about 7.

In certain embodiments, the present compounds can enhance the perceivedsweetness of a fixed concentration of a sweetener in taste tests at acompound concentration of about 50 μM, 40 μM, 30 μM, 20 μM, or 10 μM atacidic to basic pH. In certain embodiments, the enhancement factor ofthe present compounds at the lower pH is substantially similar to theenhancement factor of the compounds at neutral pH.

Furthermore, in some embodiments, the present compounds have enhancedphotostability. That is, when exposed to a light source, the compoundshave stability and are less prone to degradation. Such photostabilityand consistent sweet enhancing property under a broad range of pH'srender the compounds good candidates for use in a wide variety of foodsand beverages.

Typically, at least a sweet receptor modulating amount, a sweet receptorligand modulating amount, a sweet flavor modulating amount, a sweetflavoring agent amount, a sweet flavor enhancing amount, or atherapeutically effective amount of one or more of the present compoundswill be added to the ingestible composition, optionally in the presenceof known sweeteners, e.g., so that the sweet flavor modified ingestiblecomposition has an increased sweet taste as compared to the ingestiblecomposition prepared without the compounds of the present invention, asjudged by human beings or animals in general, or in the case offormulations testing, as judged by a majority of a panel of at leasteight human taste testers, via procedures commonly known in the field.

The concentration of sweet flavoring agent needed to modulate or improvethe flavor of the ingestible composition will of course depend on manyvariables, including the specific type of the ingestible composition andits various other ingredients, especially the presence of other knownsweet flavoring agents and the concentrations thereof, the naturalgenetic variability and individual preferences and health conditions ofvarious human beings tasting the compositions, and the subjective effectof the particular compound on the taste of such chemosensory compounds.

One application of the present compounds is for modulating (inducing,enhancing or inhibiting) the sweet taste or other taste properties ofnatural or synthetic sweeteners, and ingestible compositions madetherefrom. In one embodiment, the compounds of the present invention areused or provided in their ligand enhancing concentration(s).

In one embodiment, the present invention provides a sweet enhancingcomposition. The sweet enhancing composition comprises a compound of thepresent invention in an amount effective to enhance sweetening, e.g.,sweet flavor enhancing amount in combination with a first amount ofsweetener, wherein the sweetening is more than the sweetening providedby the first amount of sweetener without the compound of the subjectinvention.

In one embodiment, the present invention provides an ingestiblecomposition that comprises the sweet enhancing composition of thepresent invention. In certain embodiments, the ingestible composition isin the form of a food or beverage product, a pharmaceutical composition,a nutritional product, a dietary supplement, over-the-countermedication, or oral care product.

Noncomestible Products

In certain embodiments, a compound of the present invention is added toa noncomestible composition or non-edible product, such as apharmaceutical product, over the counter (OTC) product, oral careproduct, cosmetic product such as sweetened lip balms, or other personalcare product.

Over the counter (OTC) product and oral care product refer to productsfor household and/or personal use that may be sold without aprescription and/or without a visit to a medical professional. Examplesof OTC products include, but are not limited to, vitamins and dietarysupplements; topical analgesics and/or anesthetics; cough, cold andallergy remedies; antihistamines and/or allergy remedies; andcombinations thereof.

Vitamins and dietary supplements include, but are not limited to,vitamins, dietary supplements, tonics/bottled nutritive drinks,child-specific vitamins, dietary supplements, and any other suchproducts.

Topical analgesics and/or anesthetics include any topicalcreams/ointments/gels used to alleviate superficial or deep-seated achesand pains, e.g., muscle pain; teething gel; patches with analgesicingredient; and combinations thereof.

Cough, cold and allergy remedies include, but are not limited to,decongestants; cough remedies; pharyngeal preparations; medicatedconfectioneries; antihistamines and child-specific cough, cold andallergy remedies; and combination products.

Antihistamines and/or allergy remedies include, but are not limited to,any systemic treatments for hay fever, nasal allergies, and insect bitesand stings.

Examples of oral care products include, but are not limited to mouthcleaning strips, toothpaste, toothbrushes, mouthwashes/dental rinses,denture care, mouth fresheners at-home teeth whiteners, dentifrices, anddental floss.

Food and Beverage Products

In another embodiment, the present compounds are added to food orbeverage products or formulations. Examples of food and beverageproducts or formulations include, but are not limited to sweet coatings,frostings, or glazes for comestible products or any entity included inthe Soup category, the Dried Processed Food category, the Beveragecategory, the Ready Meal category, the Canned or Preserved Foodcategory, the Frozen Processed Food category, the Chilled Processed Foodcategory, the Snack Food category, the Baked Goods category, theConfectionary category, the Dairy Product category, the Ice Creamcategory, the Meal Replacement category, the Pasta and Noodle category,and the Sauces, Dressings, Condiments category, the Baby Food category,and/or the Spreads category.

In general, the Soup category refers to canned/preserved, dehydrated,instant, chilled, UHT and frozen soup. For the purpose of thisdefinition soup(s) means a food prepared from meat, poultry, fish,vegetables, grains, fruit and other ingredients, cooked in a liquid thatmay include visible pieces of some or all of these ingredients. It maybe clear (as a broth) or thick (as a chowder), smooth, pureed or chunky,ready-to-serve, semi-condensed or condensed and may be served hot orcold, as a first course or as the main course of a meal or as a betweenmeal snack (sipped like a beverage). Soup may be used as an ingredientfor preparing other meal components and may range from broths (consomme)to sauces (cream or cheese-based soups).

The Dehydrated and Culinary Food Category means: (i) Cooking aidproducts such as: powders, granules, pastes, concentrated liquidproducts, including concentrated bouillon, bouillon and bouillon likeproducts in pressed cubes, tablets or powder or granulated form, whichare sold separately as a finished product or as an ingredient within aproduct, sauces and recipe mixes (regardless of technology); (ii) Mealsolutions products such as: dehydrated and freeze dried soups, includingdehydrated soup mixes, dehydrated instant soups, dehydratedready-to-cook soups, dehydrated or ambient preparations of ready-madedishes, meals and single serve entrees including pasta, potato and ricedishes; and (iii) Meal embellishment products such as: condiments,marinades, salad dressings, salad toppings, dips, breading, battermixes, shelf stable spreads, barbecue sauces, liquid recipe mixes,concentrates, sauces or sauce mixes, including recipe mixes for salad,sold as a finished product or as an ingredient within a product, whetherdehydrated, liquid or frozen.

The Beverage category means beverages, beverage mixes and concentrates,including but not limited to, carbonated and non-carbonated beverages,alcoholic and non-alcoholic beverages, ready to drink beverages, liquidconcentrate formulations for preparing beverages such as sodas, and drypowdered beverage precursor mixes. The Beverage category also includesalcoholic drinks, soft drinks, sports drinks, isotonic beverages, andhot drinks. Alcoholic drinks include, but are not limited to beer,cider/perry, FABs, wine, and spirits. The soft drinks include, but arenot limited to carbonates, such as colas and non-cola carbonates; fruitjuice, such as juice, nectars, juice drinks and fruit flavored drinks;bottled water, which includes sparkling water, spring water andpurified/table water, functional drinks, which can be carbonated orstill and include sport, energy or elixir drinks; concentrates, such asliquid and powder concentrates in ready to drink measure. The drinks,either hot or cold, include, but are not limited to coffee or icecoffee, such as fresh, instant, and combined coffee; tea or ice tea,such as black, green, white, oolong, and flavored tea; and other drinksincluding flavor-, malt- or plant-based powders, granules, blocks ortablets mixed with milk or water.

The Snack Food category refers to any food that can be a light informalmeal including, but not limited to, sweet and savory snacks and snackbars. Examples of snack food include, but are not limited to, fruitsnacks, chips/crisps, extruded snacks, tortilla/corn chips, popcorn,pretzels, nuts and other sweet and savory snacks. Examples of snack barsinclude, but are not limited to, granola/muesli bars, breakfast bars,energy bars, fruit bars and other snack bars.

The Baked Goods category refers to any edible product the process ofpreparing which involves exposure to heat or excessive sunlight.Examples of baked goods include, but are not limited to bread, buns,cookies, muffins, cereal, toaster pastries, pastries, waffles,tortillas, biscuits, pies, bagels, tarts, quiches, cake, any bakedfoods, and any combination thereof.

The Ice Cream category refers to frozen dessert containing cream andsugar and flavoring. Examples of ice cream include, but are not limitedto: impulse ice cream; take-home ice cream; frozen yoghurt and artisanalice cream; soy, oat, bean (e.g., red bean and mung bean), and rice-basedice creams.

The Confectionary category refers to edible product that is sweet to thetaste. Examples of confectionary include, but are not limited to,candies, gelatins, chocolate confectionery, sugar confectionery, gum,and the likes and any combination products.

The Meal Replacement category refers to any food intended to replace thenormal meals, particularly for people having health or fitness concerns.Examples of meal replacement include, but are not limited to, slimmingproducts and convalescence products.

The Ready Meal category refers to any food that can be served as a mealwithout extensive preparation or processing. The ready meal includesproducts that have had recipe “skills” added to them by themanufacturer, resulting in a high degree of readiness, completion andconvenience. Examples of ready meals include, but are not limited tocanned/preserved, frozen, dried, chilled ready meals; dinner mixes;frozen pizza; chilled pizza; and prepared salads.

The Pasta and Noodle category includes any pastas and/or noodlesincluding, but not limited to canned, dried and chilled/fresh pasta; andplain, instant, chilled, frozen and snack noodles.

The Canned/Preserved Food category includes, but is not limited to,canned/preserved meat and meat products, fish/seafood, vegetables,tomatoes, beans, fruit, ready meals, soup, pasta, and othercanned/preserved foods.

The Frozen Processed Food category includes, but is not limited to,frozen processed red meat, processed poultry, processed fish/seafood,processed vegetables, meat substitutes, processed potatoes, bakeryproducts, desserts, ready meals, pizza, soup, noodles, and other frozenfood.

The Dried Processed Food category includes, but is not limited to, rice,dessert mixes, dried ready meals, dehydrated soup, instant soup, driedpasta, plain noodles, and instant noodles. The Chill Processed Foodcategory includes, but is not limited to, chilled processed meats,processed fish/seafood products, lunch kits, fresh cut fruits, readymeals, pizza, prepared salads, soup, fresh pasta and noodles.

The Sauces, Dressings and Condiments category includes, but is notlimited to, tomato pastes and purees, bouillon/stock cubes, herbs andspices, monosodium glutamate (MSG), table sauces, soy based sauces,pasta sauces, wet/cooking sauces, dry sauces/powder mixes, ketchup,mayonnaise, mustard, salad dressings, vinaigrettes, dips, pickledproducts, and other sauces, dressings and condiments.

The Baby Food category includes, but is not limited to, milk- orsoybean-based formula; and prepared, dried and other baby food.

The Spreads category includes, but is not limited to, jams andpreserves, honey, chocolate spreads, nut based spreads, and yeast basedspreads.

The Dairy Product category generally refers to edible product producedfrom mammal's milk. Examples of dairy product include, but are notlimited to, drinking milk products, cheese, yoghurt and sour milkdrinks, and other dairy products.

Additional examples for comestible composition, particularly food andbeverage products or formulations, are provided as follows. Exemplarycomestible compositions include one or more confectioneries, chocolateconfectionery, tablets, countlines, bagged selflines/softlines, boxedassortments, standard boxed assortments, twist wrapped miniatures,seasonal chocolate, chocolate with toys, alfaj ores, other chocolateconfectionery, mints, standard mints, power mints, boiled sweets,pastilles, gums, jellies and chews, toffees, caramels and nougat,medicated confectionery, lollipops, liquorice, other sugarconfectionery, gum, chewing gum, sugarized gum, sugar-free gum,functional gum, bubble gum, bread, packaged/industrial bread,unpackaged/artisanal bread, pastries, cakes, packaged/industrial cakes,unpackaged/artisanal cakes, cookies, chocolate coated biscuits, sandwichbiscuits, filled biscuits, savory biscuits and crackers, breadsubstitutes, breakfast cereals, rte cereals, family breakfast cereals,flakes, muesli, other cereals, children's breakfast cereals, hotcereals, ice cream, impulse ice cream, single portion dairy ice cream,single portion water ice cream, multi-pack dairy ice cream, multi-packwater ice cream, take-home ice cream, take-home dairy ice cream, icecream desserts, bulk ice cream, take-home water ice cream, frozenyoghurt, artisanal ice cream, dairy products, milk, fresh/pasteurizedmilk, full fat fresh/pasteurized milk, semi skimmed fresh/pasteurizedmilk, long-life/uht milk, full fat long life/uht milk, semi skimmed longlife/uht milk, fat-free long life/uht milk, goat milk,condensed/evaporated milk, plain condensed/evaporated milk, flavored,functional and other condensed milk, flavored milk drinks, dairy onlyflavored milk drinks, flavored milk drinks with fruit juice, soy milk,sour milk drinks, fermented dairy drinks, coffee whiteners, powder milk,flavored powder milk drinks, cream, cheese, processed cheese, spreadableprocessed cheese, unspreadable processed cheese, unprocessed cheese,spreadable unprocessed cheese, hard cheese, packaged hard cheese,unpackaged hard cheese, yoghurt, plain/natural yoghurt, flavoredyoghurt, fruited yoghurt, probiotic yoghurt, drinking yoghurt, regulardrinking yoghurt, probiotic drinking yoghurt, chilled and shelf-stabledesserts, dairy-based desserts, soy-based desserts, chilled snacks,fromage frais and quark, plain fromage frais and quark, flavored fromagefrais and quark, savory fromage frais and quark, sweet and savorysnacks, fruit snacks, chips/crisps, extruded snacks, tortilla/cornchips, popcorn, pretzels, nuts, other sweet and savory snacks, snackbars, granola bars, breakfast bars, energy bars, fruit bars, other snackbars, meal replacement products, slimming products, convalescencedrinks, ready meals, canned ready meals, frozen ready meals, dried readymeals, chilled ready meals, dinner mixes, frozen pizza, chilled pizza,soup, canned soup, dehydrated soup, instant soup, chilled soup, hotsoup, frozen soup, pasta, canned pasta, dried pasta, chilled/freshpasta, noodles, plain noodles, instant noodles, cups/bowl instantnoodles, pouch instant noodles, chilled noodles, snack noodles, cannedfood, canned meat and meat products, canned fish/seafood, cannedvegetables, canned tomatoes, canned beans, canned fruit, canned readymeals, canned soup, canned pasta, other canned foods, frozen food,frozen processed red meat, frozen processed poultry, frozen processedfish/seafood, frozen processed vegetables, frozen meat substitutes,frozen potatoes, oven baked potato chips, other oven baked potatoproducts, non-oven frozen potatoes, frozen bakery products, frozendesserts, frozen ready meals, frozen pizza, frozen soup, frozen noodles,other frozen food, dried food, dessert mixes, dried ready meals,dehydrated soup, instant soup, dried pasta, plain noodles, instantnoodles, cups/bowl instant noodles, pouch instant noodles, chilled food,chilled processed meats, chilled fish/seafood products, chilledprocessed fish, chilled coated fish, chilled smoked fish, chilled lunchkit, chilled ready meals, chilled pizza, chilled soup, chilled/freshpasta, chilled noodles, oils and fats, olive oil, vegetable and seedoil, cooking fats, butter, margarine, spreadable oils and fats,functional spreadable oils and fats, sauces, dressings and condiments,tomato pastes and purees, bouillon/stock cubes, stock cubes, gravygranules, liquid stocks and fonds, herbs and spices, fermented sauces,soy based sauces, pasta sauces, wet sauces, dry sauces/powder mixes,ketchup, mayonnaise, regular mayonnaise, mustard, salad dressings,regular salad dressings, low fat salad dressings, vinaigrettes, dips,pickled products, other sauces, dressings and condiments, baby food,milk formula, standard milk formula, follow-on milk formula, toddlermilk formula, hypoallergenic milk formula, prepared baby food, driedbaby food, other baby food, spreads, jams and preserves, honey,chocolate spreads, nut-based spreads, and yeast-based spreads. Exemplarycomestible compositions also include confectioneries, bakery products,ice creams, dairy products, sweet and savory snacks, snack bars, mealreplacement products, ready meals, soups, pastas, noodles, canned foods,frozen foods, dried foods, chilled foods, oils and fats, baby foods, orspreads or a mixture thereof. Exemplary comestible compositions alsoinclude breakfast cereals, sweet beverages or solid or liquidconcentrate compositions for preparing beverages, ideally so as toenable the reduction in concentration of previously known saccharidesweeteners, or artificial sweeteners.

Concentrates

According to another aspect of the invention, the compounds of thepresent invention can be provided in a concentrate formulation, e.g.,suitable for subsequent processing to produce a ready-to-use (i.e.,ready-to-serve) product.

By “a flavoring concentrate formulation,” is meant a formulation thatcan be reconstituted with one or more diluting media to become aready-to-use composition. The term “ready-to-use composition” is usedinterchangeably herein with “ingestible composition,” which denotes anysubstance that, either alone or together with another substance, can betaken orally whether intended for consumption or not. In one embodiment,the ready-to-use composition includes a composition that can be directlyconsumed by a human or animal.

The flavoring concentrate formulation is typically used by mixing withone or more diluting media, e.g., any consumable or ingestibleingredient or product, to impart or modify one or more flavors to thediluting medium. Such a process is often referred to as reconstitution.

The reconstitution can be conducted in a household setting or anindustrial setting. For example, a frozen fruit juice concentrate can bereconstituted with water or other aqueous medium by a consumer in akitchen to obtain the ready-to-use fruit juice beverage. In anotherexample, a soft drink syrup concentrate can be reconstituted with wateror other aqueous medium by, for example, a restaurant, vendor, or amanufacturer in large industrial scale to produce the ready-to-use softdrinks.

Because the flavoring concentrate formulation has the flavoring agent orflavor modifying agent in a concentration higher than the ready-to-usecomposition, the flavoring concentrate formulation is typically notsuitable for being consumed directly without reconstitution.

There are many benefits of using and producing a flavoring concentrateformulation. For example, one benefit is the reduction in weight andvolume for transportation as the flavoring concentrate formulation canbe reconstituted at the time of usage by the addition of suitablesolvent, solid or liquid.

In one embodiment, the flavoring concentrate formulation comprises acompound of the present invention; a carrier; and optionally, at leastone adjuvant. The term “as flavor modifying ingredient” denotes that thecompound of the present invention acts as a flavoring agent or a flavormodifying agent (such as a flavor enhancer) in the formulation. The term“carrier” denotes a usually inactive accessory substance, such assolvents, binders, or other inert medium, which is used in combinationwith the present compound and one or more optional adjuvants to form theformulation. For example, water or starch can be a carrier for aflavoring concentrate formulation. In some embodiments, the carrier isthe same as the diluting medium for reconstituting the flavoringconcentrate formulation; and in other embodiments, the carrier isdifferent from the diluting medium. The term “carrier” as used hereinincludes, but is not limited to, ingestibly acceptable carrier.

The term “adjuvant” denotes an additive that supplements, stabilizes,maintains, or enhances the intended function or effectiveness of theactive ingredient, such as the compound of the present invention. In oneembodiment, the at least one adjuvant comprises one or more flavoringagents. The flavoring agent may be of any flavor known to one skilled inthe art or consumers, such as the flavor of chocolate, coffee, tea,mocha, French vanilla, peanut butter, chai, or combinations thereof. Inanother embodiment, the at least one adjuvant comprises one or moresweeteners. The one or more sweeteners can be any of the sweetenersdescribed herein. In another embodiment, the at least one adjuvantcomprises one or more ingredients selected from emulsifiers,stabilizers, antimicrobial preservatives, antioxidants, vitamins,minerals, fats, starches, protein concentrates and isolates, salts, andcombinations thereof. Examples of emulsifiers, stabilizers,antimicrobial preservatives, antioxidants, vitamins, minerals, fats,starches, protein concentrates and isolates, and salts are described inU.S. Pat. No. 6,468,576, which is hereby incorporated by reference inits entirety.

The present flavoring concentrate formulation can be in a form selectedfrom, for example, liquid including solution and suspension, solid,foamy material, paste, gel, cream, and a combination thereof, such as aliquid containing a certain amount of solid contents. In one embodiment,the flavoring concentrate formulation is in the form of a liquid,including aqueous-based and non-aqueous-based. The flavoring concentrateformulation can be carbonated or non-carbonated.

The flavoring concentrate formulation may further comprise a freezingpoint depressant, nucleating agent, or both as the at least oneadjuvant. The freezing point depressant is an ingestibly acceptablecompound or agent that can depress the freezing point of a liquid orsolvent to which the compound or agent is added. That is, a liquid orsolution containing the freezing point depressant has a lower freezingpoint than the liquid or solvent without the freezing point depressant.In addition to depressing the onset freezing point, the freezing pointdepressant may also lower the water activity of the flavoringconcentrate formulation. Examples of freezing point depressants include,but are not limited to, carbohydrates, oils, ethyl alcohol, polyol,e.g., glycerol, and combinations thereof.

Nucleating agents are ingestibly acceptable compounds or agents thatfacilitate nucleation. The presence of a nucleating agent in theflavoring concentrate formulation can improve the mouthfeel of, forexample, a frozen slush and help maintain the physical properties andperformance of the slush at freezing temperatures by increasing thenumber of ice crystallization centers. Examples of nucleating agentsinclude, but are not limited to, calcium silicate, calcium carbonate,titanium dioxide, and combinations thereof.

In one embodiment, the flavoring concentrate formulation is formulatedto have a low water activity for extended shelf life. Water activity isthe ratio of the vapor pressure of water in a formulation to the vaporpressure of pure water at the same temperature. In one embodiment, theconcentrate formulation has a water activity of less than about 0.85. Inanother embodiment, the concentrate formulation has a water activity ofless than about 0.80. In another embodiment, the concentrate formulationhas a water activity of less than about 0.75.

In one embodiment, the flavoring concentrate formulation has the presentcompound in a concentration that is at least 2, 5, 10, 20, 30, 40, 50,75, 100, or more times the concentration of the compound in aready-to-use composition.

Having now generally described the invention, the same will be morereadily understood by reference to the following examples, which areprovided by way of illustration and are not intended as limiting. It isunderstood that various modifications and changes can be made to theherein disclosed exemplary embodiments without departing from the spiritand scope of the invention.

EXAMPLES Example 1—General Method for Measuring Taste ReceptorActivity—Fluo-4 Calcium Assay

Fluo-4 is a fluorescent indicator for intracellular calcium and allowsthe determination of changes in calcium concentration, in particular anincrease in response to receptor activation occurring after ligandaddition. HEK293 cells stably expressing Gα16-gustducin 44 (Gα16gust44)were used as host cells and transfected with various constructs asdescribed in examples 2-5. Black, clear-bottom 96-well plates were usedfor all assays. They were seeded the day before the assay with 8500transfected cells per well and maintained at 37° C. overnight in agrowth medium appropriate for the cells used. For HEK293 cells,Dulbecco's Modified Eagle medium supplemented with 10% fetal bovineserum was used for growth and maintenance of the HEK293 cells.

At the time of the assay, the growth medium was discarded and cells wereincubated for 1 hour (at 37° C. in the dark) with 50 μl of a calciumassay solution consisting of 1.5 μM Fluo-4 AM (Molecular Probes™,Invitrogen, US) and 2.5 μM probenecid (Sigma-Aldrich) dissolved in a C1buffer solution. C1 buffer solution contains 130 mM NaCl, 5 mM KCl, 10mM Hepes, 2 mM CaCl₂) and 10 mM glucose (pH 7.4).

After the initial 1 hour loading period, the plates were washed 5 timeswith 100 μl per well of C1 buffer using an automated plate washer(BioTek) and after washing, the cells were further incubated in 100 μlC1 buffer per well for 30 minutes at room temperature in the dark toallow for complete de-esterification of the Fluo-4-AM. The buffersolutions were discarded, the plate was washed 5 times with 100 μl C1wash buffer and finally the cells were placed in 180 μl of C1 washbuffer.

For assay reading, the plate was placed in a FLIPR (fluorescence imagingplate reader (FLIPR-Tetra, Molecular Devices), and receptor activationwas initiated following addition of 20 μl of a 10× concentrated ligandstock solution. Fluorescence was continuously monitored for 15 secondsprior to ligand addition and for 105 seconds after ligand addition(45-105 sec may be sufficient).

Receptor activation is given in relative fluorescence units (RFU) and isdefined by the following equation: Fluorescence Increase=MaximumFluorescence—baseline fluorescence, wherein the baseline fluorescencerepresents the mean fluorescence calculated for the first 10 to 15seconds prior to ligand addition.

Alternatively, Receptor activation is determined by the increase in peakfluorescence (F) normalized to the baseline fluorescence (F₀). The dataare normalized using the following equation: ΔF/F=(F−F₀)/F₀, where F isthe peak fluorescence signal and F₀ is the baseline fluorescence signal,wherein the baseline fluorescence represents the mean fluorescencecalculated for the first 10 to 15 seconds prior to ligand addition.

As a negative control, mock transfected cells were exposed to the sameconcentration of ligand and the concentration of calcium traces notcorresponding to a signal was determined. Cells with an activatedreceptor were identified by the signal (RFU or ΔF/F) being significantlyabove the negative control.

Example 2—Sweet Flavor and Sweet Flavor Enhancement Measurement UsingHuman Panelists Conducting a Paired Comparison Test

Test samples containing experimental compounds are presented in pairs tothe panelist and they are asked to determine which of the samples issweeter. The present compounds can be tested for sweet flavorenhancement in a medium with a wide range of pH values, for example, atpH of about 7.1 or about 2.8. A group of 10 to 16 or more panelists canparticipate in each test. Subjects refrain from eating or drinking(except water) for at least 1 hour prior to the test. Subjects rinsewith water several times to clean the mouth prior to testing.

Taste tests were performed with sucrose or HFCS as the sweetener in thepresence or absence of compound. A 0.2% stock solution of compound inwater with sodium bicarbonate was prepared and then this stock solutionwas diluted in the final sample to achieve the targeted finalconcentration of compound. Taste samples were also prepared in a lowsodium phosphate buffer (pH 7.1; “LSB”) lacking sucrose or HFCS toevaluate the taste of the compound alone.

Low sodium phosphate buffer consists of 0.3 mM KCl, 0.5 mM Na₂HPO₄, and0.175 mM KH₂PO₄. Sample volumes are usually 20 ml.

In one paired comparison test, the panelist is presented with twodifferent samples and asked to identify the sample which is sweeter. Thesamples within a paired comparison test are presented in a randomized,counterbalanced order. Panelists have up to a 1 minute delay betweentaste tests to clear the mouth of any tastes.

Binomial probability tables are used to determine the probability of thecorrect number of responses occurring for each test at alpha=0.05.

Example 3—Ranking Tests to Determine the Sweetness Isointensity ofSweetness Enhancers

For comparative ranking, samples of 0.5%, 1%, 1.5%, 7%, 8%, 9%, 10% and11% sucrose solutions can be prepared.

a) Sweetness Isointensity of Sweetness Enhancer in Sucrose Solutions

The sensory evaluation can be conducted using a ranking method. Samplesat ambient temperature can be randomly presented in 15 ml blind aliquots(unidentifiable by panelists). Panels consisting of 10 sweet sensitivesubjects and samples can be presented in 3 replications over 1 session.After tasting each sample, the mouth is rinsed thoroughly with water atambient temperature prior to tasting the next sample. Panelists can bepresented with 7%, 8%, 9%, 10%, 11% sucrose samples and a sixth sampleof 7% sucrose with a sweetness enhancer in a concentration near itssweetness detection threshold. They can be asked to rank the samplesfrom low to high with respect to perceived sweet taste. R-indices can becalculated for 7% sucrose with the sweetness enhancer versus 7%, 8%, 9%,10% or 11% sucrose.

b) Near Threshold Sweetness Isointensity of Sweetness Enhancer in Water

The sensory evaluation can be conducted using a ranking method. Samplesat ambient temperature can be randomly presented in 15 ml blind aliquots(unidentifiable by panelists). Panels consisting of 10 sweet sensitivesubjects and samples can be presented in 3 replications over 1 session.After tasting each sample, the mouth is rinsed thoroughly with water atambient temperature prior to tasting the next sample.

Panelists can be presented with either 0.5% and 1% sucrose or 1% and1.5% sucrose and a third sample of water with a sweetness enhancer in aconcentration near its sweetness detection threshold. They can be askedto rank the samples from low to high with respect to perceived sweettaste.

R-indices can be calculated for the sweetness enhancer in water versuseither 0.5% and 1% sucrose or 1% and 1.5% sucrose. The R-index is astatistic obtained by an analytical procedure based on signal detectionand is a short-cut method for determining the proportion of subjectschoosing one sample over another (see O'Mahony, 1992, J. Sens. Stud.,7:1-47). From ranking-style sensory tests, a matrix of responses (seetable 3 below) is constructed such that each cell contains the number oftimes a given sample was ranked at a particular location.

TABLE 3 Position 1 Position 2 Sample (least sweet) (most sweet) Position3 Sample X A B C Sample Y D E F Sample Z G H I

From this matrix, the R-index can be calculated according to thefollowing equation:

R-index(X vs. Y)=A(E+F)+B(F)+0.5((A*D)+(B*E)+(C*F))(A+B+C)*(D+E+F).

Essentially, the R-index is a measure of difference between two samples.The R-index has a chance level of detection of 50%. Thus, when comparingtwo samples, the derived R-index must be significantly different from50% in order for them to be considered different. The critical value isthe statistically relevant value that the derived R-index must deviatefrom (i.e., greater or less than) in order to be considered significant.

An R-index greater than the higher critical value means that thesweetness enhancer sample is significantly sweeter than the sucrosesample. An R-index not significantly different from the critical valuemeans that the sweetness enhancer sample has an equivalent sweetness tothe compared sucrose sample. An R-index below the lower critical valueindicates that the sucrose sample is sweeter than the sweetness enhancersample.

All patents, patent applications, provisional applications, andpublications referred to or cited herein are incorporated by referencein their entirety, including all figures and tables, to the extent theyare not inconsistent with the explicit teachings of this specification.

It should be understood that the examples and embodiments describedherein are for illustrative purposes only and that various modificationsor changes in light thereof will be suggested to persons skilled in theart and are to be included within the spirit and purview of thisapplication.

1. A composition comprising an isolated sweet taste modulator compoundselected from the group consisting of the compounds in Table 1 and Table2, and derivatives thereof, wherein said composition further comprisesat least one sweetener.
 2. The composition of claim 1, wherein theisolated sweet taste modulator compound is selected from the groupconsisting of the compounds in Table 3, and derivatives thereof.
 3. Thecomposition of claim 1, wherein the isolated sweet taste modulatorcompound has a core of

C(C(C(C(:C(:C(:C(C(OC[*:9])[*:8])[*:7])[*:6])[*:5])[*:4])[*:3])[*:2])[*:1],wherein R1-R8 are selected from the substituents listed in Table 1-A. 4.The composition of claim 1, wherein the isolated sweet taste modulatorcompound has a core of

c1c(O[*:3])c([*:4])c([*:6])c(C(C[*:1])[*:2])c1 [*:5], wherein R1-R6 areselected from the substituents listed in Table 1-B.
 5. The compositionof claim 4, wherein the isolated sweet taste modulator compound has aSMILES structure of c12c(OC [C@@H](C1=O)Cc1cc(c(cc1)O)O)cc(cc2OC)O. 6.The composition of claim 1, wherein the isolated sweet taste modulatorcompound has a core of

C(:C(:C(:C(O[*:5])[*:4])[*:3])[*:2])[*:1], wherein R1-R5 are selectedfrom the substituents listed in Table 1-C.
 7. The composition of claim6, wherein the isolated sweet taste modulator compound has a SMILESstructure selected from the group consisting of[C@H]1(c2cc(c(c(c2)O)OC)O)[C@@H](Cc2c(O1)cc(cc2O)O)O; COc1cc(ccc1O)[C@H]1 [C@@H](Cc2c(cc(cc2O1)O)O)O; COc1c(ccc(c1OC)O)[C@@H]1Cc2ccc(cc2OC1)O; c1(cc(c(c(c1)O)OC)O)/C═C\c1cc(cc(c1)O)O;[C@@H]1(c2cc(c(cc2)OC)O)[C@H](Cc2c(O1)cc(cc2O)OC)O; andCOc1ccc(c(c1OC)O) [C@H]1Cc2ccc(cc2OC1)O.
 8. The composition of claim 1,wherein the isolated sweet taste modulator compound has a core ofC(:C1:C([*:4]):C([*:3]):C([*:2]):C([*:6]):C:1[*:5])[*:1], wherein R1-R6are selected from the substituents listed in Table 1-D.
 9. Thecomposition of claim 8, wherein the isolated sweet taste modulatorcompound has a SMILES structure selected from the group consisting ofCOc1cc(ccc1O)[C@@H]1[C@@H](Oc2ccc(cc2O1)[C@H]1[C@H](C(═O)c2c(cc(cc2O1)O)O)O)CO;c12c(O[C@H]([C@@H]1CO)c1cc(c(cc1)O)OC)c(ccc2[C@@H]1Oc2c(C(═O)C1)c(cc(c2)O)O)O; and COc1cc(ccc1O)[C@H]1 [C@H](c2c(ccc(c2O1)O)[C@H]1[C@@H](C(═O)c2c(cc(cc2 O1)O)O)O)CO.
 10. The composition of claim 1,wherein the isolated sweet taste modulator compound has a core of

C(:C:C(:C(C[*:5]):C(:C[*:1])[*:2])[*:4])[*:3], wherein R1-R5 areselected from the substituents listed in Table 1-E.
 11. The compositionof claim 10, wherein the isolated sweet taste modulator compound has aSMILES structure selected from the group consisting ofCc1cc2c(c(c1)O)C(═O)c1c(cc(cc1O)O)C2=O; andCc1cc2c(c(c1)O)C(═O)c1c(cccc1O)C2.
 12. The composition of claim 1,wherein the isolated sweet taste modulator compound has a core of,C(:C(:C[*:2]):C(:C(C[*:5])[*:4])[*:3])[*:1], wherein R1-R5 are selectedfrom the substituents listed in Table 2-A.
 13. The composition of claim1, wherein the isolated sweet taste modulator compound has a core of

c1c([*:2])c([*:1])c([*:5])c([*:4])c1[*:3], wherein R1-R5 are selectedfrom the substituents listed in Table 2-B.
 14. The composition of claim13, wherein the isolated sweet taste modulator compound has a SMILESstructure selected from the group consisting ofCOC1=C(O)C═C(C=C1)[C@@H]1CC(═O)C2=C(O)C═C(O)C=C2O1;COC1=CC═C(C=C1)C1CC(═O)C2=C(O1)C═C(O)C=C2O;OC1=CC═C(C=C1)C1CC(═O)C2=C(O1)C═C(O)C=C2O;COC1=CC═C(C2COC3=CC(O)═CC=C3C2)C(O)=C1;COC1=C(O)C═C(CC2COC3=CC(O)═CC(O)=C3C2=O)C=C1;COC1=CC(O)=C2C(═O)CC(OC2=C1)C1=CC(O)═CC(O)=C1;COC1=C(O)C=C2C(CC22COC3=CC(O)═CC(O)=C3C2=O)=C1;COC1=C(O)C(OC)═C(C=C1)C1COC2=CC(O)═CC=C2C1; c12c(c(c(cc2O)OC)O)OC[C@@H](C1=O)Cc1ccc(cc1)O; andCOC1=C(O)C═C(CC2(O)OC3=C(C═CC(O)=C3)C2=O)C=C1.
 15. The composition ofclaim 1, wherein the isolated sweet taste modulator compound has a coreof

C(:C(:C(:C(:C[*:3])[*:4])[*:5])[*:2])[*:1], wherein R1-R5 are selectedfrom the substituents listed in Table 2-C.
 16. The composition of claim15, wherein the isolated sweet taste modulator compound has a SMILESstructure selected from the group consisting of COC1=C(O)C(O)═C(C)C=C1O;and COC(═O)C1=C(O)C═C(O)C=C1O.
 17. The composition of claim 1, whereinthe isolated sweet taste modulator compound has a core of

C(c1c(O[*:1])c([*:2])c([*:3])c([*:4])c1[*:5])[*:6], wherein R1-R6 areselected from the substituents listed in Table 2-D.
 18. The compositionof claim 1, wherein the isolated sweet taste modulator compound has acore of

C(c1c([*:3])c([*:2])c([*:6])c([*:5])c1[*:4])[*:1], wherein R1-R6 areselected from the substituents listed in Table 2-E.
 19. The compositionof claim 18, wherein the isolated sweet taste modulator compound has aSMILES structure selected from the group consisting ofCOC1=CC(═CC=C1O)C1OC2=CC═C(C=C2OC1CO)C1OC2=CC(O)═CC(O)=C2C(═O)C1O; andCOC1=C(O)C═COC═C/C2=CC(O)═CC(O)=C2)C=C1O.
 20. The composition of claim1, wherein the at least one sweetener is selected from natural caloricsweeteners, natural high-potency sweeteners, and synthetic sweeteners.21. A flavoring concentrate formulation comprising a composition ofclaim 1 and a carrier.
 22. An ingestible composition comprising acomposition of claim 1 and an acceptable carrier for ingestion.
 23. Theingestible composition of claim 22, which has an enhanced sweet taste ascompared to an ingestible composition that does not have a compound fromTable 1 and Table 2, or a derivative thereof, but is otherwise the same.24. The ingestible composition of claim 22, wherein the ingestiblecomposition is a food, beverage, pharmaceutical, nutraceutical, tobacco,or oral hygiene/cosmetic product.
 25. A method of increasing orenhancing sweet flavor, comprising using a composition of claim
 1. 26. Amethod of modulating a sweet receptor and/or its ligand, comprisingusing a composition of claim
 1. 27. (canceled)